Vacation Rentals By Owner In Islamorada, FL

Monthly rentals only, no split months, thank you.brDay 1, of the month , to end of the month.brbrWelcome to, GULFVIEW 150, ISLAMORADA, WHITE MARLIN BEACHbrSports Fishing Capital Of The World br3200 sq ft. home , with brand new private poolbrbr5 minute walk to White Marlin Beach, from home ! br Members only, private key fob entry, to access beach.brbrLower Matecumbe, White Marlin Beach, ISLAMORADA, brTri Level 4 Bedroom, 3 Bath home, sleeps 8 to 10,brwith pool.brYou will enjoy the beautiful spacious 800 sqf with 16.5 foot vaulted ceiling main room masterfully crafted by gifted carpenters with an open kitchen, newer appliances , induction Miele cooktop and *reverse osmosis drinking water filtration , complete with 70 TV internet, cable tv, a pool table, KMP L shape sofa, beautiful Tommy Bahama dining room table that expands to seat 8 - all opening up to 9'x50' , back veranda with plenty of seating for your whole group! brA wrap around walk way all on the 2nd level, of this beautiful 3200sq.ft under A/C. over 5200+sq ft. under roof including 900 sq ft garage and it's covered porches.brThe stunning 700sqft master bedroom suite, on the 3rd level, boasts its own balcony with seating. br brDock your boat, at the new 53' dock with multiple electrical outlets and 3 water hoses making boat maintenance easy . The property also has a natural gravel ramp for use of water toys - New Commercial Manitowac Ice machine and chest freezer, in the garage, to support your fishing needs - Outdoor shower at dock- New quality fish cleaning Station, with storage and shade. br*Weber gas grill and Blackstone grill 36 inches * Tournament rated Ping pong table- Security cameras protect dock & front parking.brNewly renovated downstairs apartment Mahi-Mahi Suite) with separate A/C, full kitchen. Living room, with Scan Design queen sleeper sofa- king size bed in bedroom, 55 TV and table for 4 . It's own patio with outside table and bar.brbrA short 3 minute boat ride, takes one into Florida Bay, another quick 3-5 min run and to the ocean and theSports Fishing Capital of the World via channel 5..brTake a 1.5 block stroll up Gulfview Drive, or ride any the 6 included bikes to private White White Marlin Beach(*best beach in the keys), have a Bar-b-que (grills, tables Adirondack chairs, all provided at the beach) go for a swim and catch the beautiful sunsets, not to be missed!brPlenty to do for the sports enthusiast, ecotourist, & the food enthusiast. The home is unique to the Florida Keys, with its 16.5' vaulted beamed ceilings in the main room with open and full wrap around balconies. 3rd floor features a massive 500 sg ft. master bedroom (20x25) with 14 ft beamed ceilings, a 65 TV and its own wrap around balcony. There is so much more we could list about this amazing home! brYou will love this home, that captures what the Florida Keys paradise living is all about. br We welcome you, to come and make beautiful long lasting memories.brbr*Close to Fine Dining br*The Best Sport Fishing in the KeysbrbrbrLocated between Miami & Key WestbrbrKey west Airport 1.5 hrs away, great day trip.brMiami Airport 1.5 hrsbrFort Lauderdale Airport 2 hrs

3200sqft Masterpiece Home, Fishing Paradise ,Waterfront, Beach, Pool, Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$793.92

Summary:brbrUnique property in the heart of Islamorada, ideal for groups and families traveling together. Enjoy rare access to a private boat basin and fishing jetty just steps away—perfect for sunset views and relaxing by the water. Two separate living spaces offer privacy and flexibility while still staying connected. Walk to restaurants, shops, and breweries, then unwind in a peaceful setting.brbrbrbrThe Space:brbrThis rental includes two separate, fully private living spaces—one upstairs and one downstairs—with separate entrances and no interior connection. It’s ideal for groups and families who want to stay together while still having their own space.brbrbrbrUpstairs (second floor):brbr● 2 bedrooms / 2 bathroomsbrbr● Both bedrooms feature King bedsbrbr● Full kitchen + living areabrbrbrbrDownstairs (first floor):brbr● 2 bedrooms / 2 bathroomsbrbr● Primary: Queen bed + en suite bathroombrbr● Guest room: King bed + separate bathroombrbr● Full kitchen + living areabrbrbrbrNote: no closets or dressers—luggage racks and hanging space providedbrbrbrbrGuests also enjoy a private courtyard with seating, grill, and private laundry for your group’s use.brbrbrbrThis duplex is part of a quiet, wooded waterfront property spanning the bay side of the Florida Keys. While the spaces are courtyard-facing (no direct ocean views), guests have full access to the property, including a boat basin and fishing jetty just a short walk away—perfect for sunsets and relaxing by the water.brbrbrbrGuest Access:brbrGuests have full access to both the upstairs and downstairs units. The courtyard, grill, and laundry area are private to your group and shared only between the two spaces.brbrbrbrThe remaining property grounds—including the boat basin, fishing jetty, and waterfront areas—are shared with a small number of other units on the property.brbrbrbrParking is available on-site for up to 4 vehicles. Self check-in is provided via a keypad for a smooth and flexible arrival.brbrbrbrThe Neighborhood:brbrLocated at Mile Marker 82.5 in the heart of Islamorada, this property is in one of the more walkable areas in the Upper Keys. You’re just steps from local shops and a short walk to popular restaurants, bars, and the well-known Islamorada Beer Company.brbrbrbrDespite being close to everything, the property itself is tucked away in a quiet, wooded setting—offering a more relaxed and private feel than most nearby stays.brbrbrbrA detailed guestbook is provided with our favorite recommendations for dining, drinks, and local activities.brbrbrbrGetting Around:brbrWhile this area of Islamorada is more walkable than most in the Keys, we recommend having a vehicle to fully explore nearby attractions, beaches, and surrounding areas.brbrbrbrFor shorter trips, many restaurants, shops, and local spots—including Islamorada Beer Company—are within walking distance. Biking is also a great option, and rentals are available nearby.brbrbrbrOther Things to Note:brbr● Maximum occupancy: 8 guestsbrbr● Two separate units (upstairs + downstairs) with NO interior connectionbrbr● Parking available for up to 4 vehiclesbrbr● COURTYARD VIEW (no direct ocean view), with full access to the boat basin and fishing jettybrbrbrbrBoat Basin Access (Optional)brbr● Dockage available for up to TWO vessels up to 24’ MAX (with engine)brbr● Space is shared and not assigned (placement may vary)brbr● Boat ramp available for vessels up to 20’ MAXbrbr● Larger boats cannot be accommodatedbrbr● Marina waiver required prior to arrivalbrbr● Trailer parking available on-sitebrbr● NO JET SKISbrbrbrbrCancellation Policybrbr● 100% refund: 60+ days before check-inbrbr● 50% refund: 30–60 days before check-inbrbr● No refunds within 30 daysbrbrbrbrTravel insurance is strongly recommended.brbrbrbrInteraction with Guests:brbrWe provide self check-in for a smooth and flexible arrival, but we’re always available if you need anything during your stay. We’re local and happy to help with recommendations, questions, or anything that comes up.- Sean

Sleeps 8 | Sunset + Boat Basin | Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$445.98

Welcome to paradise! Completely remodeled and immaculately maintained... Bungalow Blue is nestled away in the quiet quaint Shady Palms community of Islamorada MM76, Lower Matacumbe.brIf you're looking to relax and unwind while also being in close proximity to enjoy the best Islamorada has to offer, this is the place for you! brIdeally situated next to the community heated pool shared with only 6 other bungalows, down the street from the private boat ramp/dock, and surrounded by palm trees and tropical native landscaping, you'll truly feel you're in paradise.brEnjoy the Florida Keys lifestyle in the landscaped back yard, play a game of corn hole or jump on the beach cruisers for a short bike ride to Robbie's famous marina to feed the giant tarpon, water sport rentals, and enjoy drinks, food, and shopping.brHave your own boat(Under 26') Enjoy our free/no crowds boat launch providing direct access to the east coast waters.brbrBungalow Blue offers:br 2 bedrooms w/ queen bedsbr Newly updated bathbr New kitchen w/ stainless and granitebr Living roombr Washer/dryerbr Central A/Cbr High speed Internet & WiFibr 3X Smart Flat screen TV'sbr BBQbr Corn Hole and gamesbr 2X Beach Cruiser bikesbr Private boat rampbr Beach Chairs/Towelsbr Founders Park free accessbr Private yard w/ picnic table/Adirondack chairsbr Spacious new front porch w/ 2X umbrellas and chairsbr Hurricane impact windows and doorbrbrYou'll find a welcome packet upon arrival that includes recommendations for local dining and recreational activities. Islamorada, known as the Sportfishing Capital of the World, lends itself to some of the most famous marinas, including Bud & Mary's, only a 5 minute drive from your bungalow, and home to a fleet of charter boats and captains. brWhether you want to fish, snorkel, dive, kayak, paddle-board, or just take a cruise to the sand bar, there are multiple rental opportunities available in close range. 15 minutes north, you'll find Founders Park known as The Gem of Islamorada which offers outdoor recreation, tennis, aquatics, sports events, and a lovely beach for snorkeling(free access with copy of lease). Centrally located in the Keys allows you to day trip to Key West in 1.5 hours, or north to Key Largo in 45 minutes. Disclosure: there are two security cameras, one located on the exterior front porch and one on the back of the property solely for security purposes. brPlease feel free to reach out with any questions you may have as we are always here to help! We hope you will come visit and get to love Islamorada and our bungalow as much as we do!br- Yasmin & Joe Bartolomei

Islamorada retreat Bungalow Blue w/ heated pool, Bikes, BBQ, amenities galore!

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$694.4

You won't be disappointed once you arrive at Paradise Shores. This completely remodeled Venetian Shores 4 BD / 3 BA canal front home is perfect for families and guests. Upstairs are 2 bedrooms, 2 baths, a gorgeous kitchen, a spacious living room, an expansive porch for sitting and outside dining, a built-in BBQ, and full laundry facilities. Downstairs you will find 2 bedrooms, 1 bath, laundry facilities, a living area, and a kitchen. Step outside and enjoy the maintenance-free yard, including the oversized coral rock Spa, coral rock fire pit, 70' of dockage, fish cleaning station, boat lift, and luxurious landscaping. Conveniently located close to many well-known restaurants, marinas, breweries, boutiques, attractions, dive shops, hospitals, groceries, and movies. Approximately 1 1/2 hours from Miami, you could be in Key West for a day trip in the same amount of time. Boating access is superb. Snake Creek will take you to the Atlantic in minutes or to the Bay to catch the fabulous Florida Keys sunsets. You will have access to Founders Park to launch your boat, swim at the beach or Olympic size pool, play tennis, basketball, and walking paths. Call us today to get started on your next Keys Vacation! br

PARADISE SHORES

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1099.46

In the exclusive canal enclave of Venetian Shores with prime location between Florida Bay & the Atlantic, this 2-level Keys retreat pairs serious boating access with an epic outdoor scene. Dockage w/ power welcomes boats up to 45ft, there’s a temp-controlled pool & spa and pro grade outdoor kitchen set in a tropical paradise. With the Jimmy Buffett Suite below, the Hemingway Suite above and EV charger, bikes + water gear you’ll find perfection at a property built for serious time on the water.brbrbrbrThe SpacebrbrAhhh . . . The Florida Keys! In Venetian Shores days start on the deep-water canal and wind down beside the pool and spa at this tropical retreat. Inside, each level serves as a complete home, joined by an exterior staircase and reserved for your group alone. The Jimmy Buffett Suite on the ground level holds a spacious bedroom with a king bed and bunk beds, a full bath, a stocked kitchen, and a relaxed living room facing the canal. Just outside, a private outdoor shower sits among the palms for rinsing off after the pool or a day on the boat.brbrThe Hemingway Suite above brings more light and views, with a second full kitchen, another living area, and 2 bedrooms. The signature bedroom holds a King bed, and the guest room offers 2 Twin XL beds suited to adults or older children. Furnishings and artwork throughout the property are distinctly Florida Keys, chosen by the owner to reflect Islamorada’s boating culture and island history.brbrProperty Sleeping ConfigurationbrbrBedroom 1, Lower level: King bed + Twin-over-Twin bunkbrbrBedroom 2, Upper level: King bedbrbrBedroom 3, Upper level: 2 Twin XL bedsbrbrOf course, the main event at this tropical enclave is the outdoor living area and its long list of amenities! Along the canal, the pool terrace runs the length of the house. The temperature-controlled pool is heated when the weather cools and chilled in summer, with a separate spa that comes up to temperature quickly after a run offshore. A shaded lounge area faces the water beside a professional grade outdoor kitchen and bar. The kitchen is equipped with a Blaze grill and commercial ice maker, under-counter refrigeration and a dedicated bar refrigerator, plus a large television so guests can swim, grill, watch the game, and pour sunset cocktails without leaving the deck. Orchids, exotic palms, and fruit trees frame the pool and canal under landscape lighting after dark. In cooler months, a wood-burning fire pit with stacked wood turns the canal edge into the spot for boat drinks at the end of the night.brbrFor anglers and boaters, the deep-water canal is the defining advantage with direct runs toward Florida Bay and the Atlantic. Dockage with power accommodates boats up to about 45 feet, and the on-site bait freezer in the laundry room keeps bait and fresh catch ready when you are. Fishing rods are provided for canal casting, and a kayak offers a quieter way to explore the mangroves. Six bicycles are provided for rides through Venetian Shores and into Islamorada between days on the boat and time by the pool. And our EV charger ensures you'll be ready for any day trip throughout the Keys, no worries about needing to find a charging station offsite. brbrThe AreabrbrLocated at mile marker 86, Venetian Shores is known for its canal network and central location between Florida Bay and the Atlantic. From here, you have prime access to offshore fishing, sandbars, and the restaurants and marinas of the Upper Keys.brbrOf NotebrbrThis is a premium home in a highly sought area, priced for guests who expect a Keys stay that feels closer to a private resort than a typical rental. The entire property is reserved for one reservation, never split between groups, which preserves privacy, space, and the sense that every detail has been considered before you arrive.

Venetian Shores Waterfront with Ocean Access, Pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$490.17

Boat slip #13 is included in this rental.brOcean view property in the Village of Islamorada located in the Florida Keys at Mile Marker 85. The property is in a gated community filled with quaint streets and walking paths throughout the perfectly manicured grounds. A heated/cooled pool cascading over a 52' beach front property overlooking the Atlantic Ocean. Enjoy the convenience of having your private dock for a 31' boat with electricity and water included. Boat slip #13 is just steps away from a refreshing dip in the pool.brbrThis home features high ceilings both upstairs and down and an open floor plan on the first floor. The kitchen is well-equipped with granite counters, stainless steel appliances and adjoins a comfortable dining area and living room. The dining area includes bar seating for two and a dining table for four and the living room is equipped with a sectional sofa with a pull-out-bed, an accent chair, coffee table and a flat screen. Hardwood floors throughout. brbrThe master suite upstairs features a king size bed, flat screen tv and a private bathroom with a walk-in shower. Additionally, the master suite has a private balcony. The guest suite features one queen bed, a pull-out sofa, closet, private bathroom with walk-in-shower and a private balcony. A stacked washer and dryer are located on the second floor for the guest's convenience.brbrbrNote: I also have a 4-bedroom rental home with a boat dock included on the front row just across from the pool with a full view of the ocean. VRBO Listing 359378

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$1257.59

Welcome to One Ten Palms! brbrEscape to paradise at this private oceanfront estate in Islamorada, where the laid-back spirit of the Keys meets resort-style comfort. Set on more than two acres of lush tropical grounds, the property is graced with 110 swaying palms and 250 feet of natural oceanfront beach, creating a sanctuary that blends relaxation, privacy, beauty, and a rich touch of Florida Keys history.brbrThis 3-bedroom, 3-bathroom residence is thoughtfully designed in a coastal-inspired style and filled with natural light. Spacious interiors include a fully stocked kitchen with all your cooking essentials, a dining area with seating for ten, and two inviting living areas. The open floor plan flows seamlessly to the pool deck and covered porch, allowing indoor and outdoor living to merge with ease.brbrAccommodating 8 to 10 guests, the home features a well-appointed master suite with a king bed and ensuite bath complete with dual vanities, a soaking tub, separate shower, and private water closet. A second bedroom with two queen beds shares a Jack-and-Jill bath with the third guest room, which is furnished with a queen bed plus a twin with trundle—offering both comfort and flexibility for families and groups of friends. An additional full bathroom is conveniently located near the main living area.brbrStep outside and discover your own private paradise, where the raw, eclectic beauty of Islamorada surrounds you. The heated and chilled pool ensures year-round enjoyment, while the Weber and Green Egg grills make it easy to prepare a surf-and-turf dinner to savor outdoors. Hammocks tucked between the palms sway gently in the breeze, creating the perfect spot for an afternoon nap or a quiet escape with a good book. brbrBeyond the pool deck, the natural beach invites both adventure and relaxation. Launch a kayak or paddleboard directly from the sand and glide across turquoise waters alive with schools of tropical fish, diving pelicans, and the occasional stingray or sea turtle. For those who prefer to keep their toes in the sand, the shoreline offers plenty of simple pleasures—whether it’s sinking into an Adirondack chair, building sandcastles, or playing beach games under the sun.brbrAs the day winds down, the fire pit becomes the heart of the property. Gather with a cocktail in hand and watch the sky transform into fiery orange and soft pink before melting into the unmistakable shades of purple that gave Islamorada its name. Derived from the Spanish words “Isla Morada,” meaning “Purple Islands,” it’s a nightly reminder of the beauty and history woven into this special place.brbrAdding to its allure is the estate’s remarkable history. Purchased in 1937, it has been lovingly passed down through the same family for generations. At that time, Islamorada was a quiet, remote village where life moved at a slower pace and each day reflected the simple rhythms of island living. The original Pink House once stretched across 12 acres from ocean to bay and is one of only 34 homes built by the Red Cross after the devastating 1935 hurricane, making it a treasured piece of Keys history. (Please note, the pink house is not accessible to guests.) In 2011, the blue house was built, blending modern amenities with the estate’s storied roots. Today, the property stands as both a sanctuary and a story, inviting guests to experience the Keys not just as visitors, but as part of its living history.brbrLocated in the heart of Islamorada, guests are just minutes from local treasures—art galleries, boutique shops, breweries, and waterfront restaurants serving live music and the freshest catch of the day. Known as the Sportfishing Capital of the World, Islamorada draws anglers from around the globe to chase everything from offshore sailfish and mahi-mahi to backcountry tarpon, bonefish, and snook. brbrFor added convenience, concierge-style services can be arranged to elevate every aspect of your stay. Daily housekeeping and pre-arrival grocery delivery ensure effortless comfort, while fresh seafood delivery brings the flavors of the Keys straight to your table. Recreational equipment rentals, including bikes and golf carts, make it easy to explore the island at your own pace. Our team can also secure dinner reservations at some of Islamorada’s most beloved restaurants, fishing charters right out of Bud N’ Mary’s Marina, or private excursions such as snorkeling at Alligator Reef, eco-tours through the mangroves, or a sunset cruise across Florida Bay. Whatever your vision of paradise looks like, we’ll take care of the details so you can simply enjoy.brbrPerfect for family vacations, romantic getaways, milestone celebrations, or gatherings of friends, your stay here will be nothing short of unforgettable.brbrReservation Deposit & Cancellations: A reservation deposit equal to one-half (50%) of the total reservation amount is due at the time of booking. TENANT shall be entitled to a refund of the one-half (50%) reservation deposit, less any non-refundable fees, if the reservation is cancelled at least 60 days prior to the occupancy date. The remaining balance, including any required security deposit, is due no later than 60 days prior to the occupancy date. If the cancellation occurs within 60 days of the occupancy date, the full reservation amount shall be non-refundable. If the booking is made less than 60 days prior to the occupancy date, the full reservation amount shall be due at the time of booking, and TENANT shall not be entitled to a refund of any amounts paid in the event of cancellation. As an exception to the foregoing, TENANT shall be entitled to a refund of all amounts paid if COASTAL re-rents the property for the same amount and for the full rental period. If the property is re-rented for fewer days or at a lower rate, COASTAL may deduct from the refund the difference between the total amount due under TENANT’s original reservation (including all taxes and fees) and the amount received from the subsequent rental. brbrInstant quote prices and calendar availability are subject to change without notice and are not guaranteed. To confirm pricing and availability, please contact Coastal Vacation Rentals of the Florida Keys and speak with one of our associates.brbrVacation Rental License: 26-4002

One Ten Palms ~ Charming Islamorada Beachfront Home with Heated Pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$942.77

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

Minutes to Library Beach Park! 2 Villa w/ Living Area | Free Onsite Parking

Islamorada, Florida, United States

Bed

Bath

Sleeps

$330.79

Embrace island life in the heart of the Florida Keys! Relax on the private beach or rent a charter for world-famous sport fishing adventures.brbrThis pool-view first-floor studio features a queen bed and a twin sleeper sofa and sleeps up to 3 guests. The unit includes a convenient kitchen, perfect for preparing quick meals on the balcony with stunning resort and ocean views. Linens, towels, and free WiFi are provided for your comfort.brbrCaloosa Cove Resort and Marina offers amenities like a heated pool, beach area, and General Store. For adventure seekers, charter boats are available at our on-site marina.brbrGetting around is easy with Caloosa's free transportation app, and the Caloosa KeyCard offers free access to Founders Park, a 25-acre haven with sandy beaches and a saltwater swimming area.brNote: Guest passes to Founders Park do not include pool use.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

Condo

Flip-Flops & Sunshine: Islamorada Studio Escape

Islamorada, Florida, United States

Bed

Bath

Sleeps

$418.53

This one-bedroom den suite in beautiful Islamorada offers the perfect blend of comfort and adventure. It has one queen bed, a queen sleeper sofa, a full sleeper sofa, plus two full bathrooms, and plenty of space to relax after your day in the Florida Keys sun.brbrWake up and decide how to spend the day:brRelax by the heated pool or sunbathe on the private beach.brHead out on a fishing charter from the on-site marina and reel in the day's catch.brExplore Founders Park with your Caloosa KeyCard for free access to sandy beaches and a saltwater swimming area. (Note: Guest passes to Founders Park do not include free use of the pool)brbrGetting around is a breeze with Caloosas free transportation app, which allows you to explore downtown and nearby dining options.brbrCaloosa Cove Resort offers stunning ocean views, swaying palm trees, and all the amenities you need, including a general store for those last-minute beach essentials.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

Apartment

Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

Islamorada, Florida, United States

Bed

Bath

5

Sleeps

$329.6

Nestled on the second floor with breathtaking ocean views, this studio is the perfect retreat for a cozy getaway in the heart of Islamorada. Comfortably accommodating up to 3 guests, the suite features a queen-size bed, a twin sleeper sofa, and a full bathroom.brbrYour stay includes access to the fantastic amenities at Caloosa Cove Resort and Marina. Unwind by the heated pool, soak up the sun on the beach, and enjoy the laid-back Keys lifestyle. Need essentials The General Store has you covered, and complimentary Wi-Fi keeps you connected. The on-site marina offers Charter Boats and boat slip rentals for thrill-seekers, letting you dive into world-class sport fishing and aquatic adventures.brbrExploration is easy with Caloosa's free transportation app, and the Caloosa KeyCard provides free access to Founders Park, a 25-acre paradise with sandy beaches, a saltwater swimming area, and plenty of room to relax and play. Please Note: Guest passes to Founders Park do not include pool use.brbrDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

Apartment

Tide & Seek: Oceanview Studio Escape in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$632.33

Peaceful Palms 2 is a brand-new 3-bedroom, 3-bathroom townhome in Islamorada—bright, breezy, and designed for easygoing Keys living. With a spacious layout, fresh coastal style, and all the extras to keep everyone entertained, this spot is perfect for your next island escape.brbrInside, the open-concept living area is great for kicking back after a day on the water. Each bedroom is cozy and welcoming, and with three full bathrooms, everyone has room to get ready without the wait. Downstairs, a dedicated game room brings the fun with a pool table, foosball table, and a classic Pac-Man machine—perfect for kids, teens, or just letting loose.brbrStep outside and enjoy access to a shared pool and dockage, whether you're bringing a boat or simply love being near the water. We've also included two paddleboards so you can explore the calm backwaters or paddle along the shoreline at your own pace. And if you're driving an electric vehicle, there's an EV charger on-site for added convenience.brbrWhether you're here to fish, paddle, unwind, or just soak up that laid-back island vibe, Peaceful Palms 2 is the perfect home base for making the most of your time in Islamorada.brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Discover Peaceful Palms 2 in Islamorada—spacious 3-bedroom condo with pool access!

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$16643.24

Intention. Attention to Detail. Expectation of Outcome. From the moment you step through the gilded entryway you immediately feel something different. Inside, the marriage of old world opulence with contemporary comfort is the very definition of a European Transitional French Château. Outside, aquamarine skies above hold the azure waters below in a timeless cerulean embrace. Slide open the telescoping doors and you’ve now combined the refined with the divine. This is the Magnum Opus of Alchemy.brbrWelcome to Chateau on the Ocean. It is the special touches that truly make this property remarkable. Now you may be asking why a Chateau, why here Well, everything happens for a reason, therefore do everything with purpose. Allow us to give you a guided tour with a brief history lesson thrown in the mix. brbrbrbrLineagebrbrbrOriginally a Latin term for a fortified castle, `château` evolved during the Renaissance into a refined manor. brbrMoving away from dark military structures, French nobles embraced Italian classical ideals: aesthetics, symmetry, art, and harmony with nature adapted to French tastes, climate, and traditions. brbrThis resulted in the genesis of a distinctive Franco-Italian hybrid; the elegant, picturesque Loire châteaux. Born in the early 1500s this is the version we know to this day. So profound was the movement that Leonardo Da Vinci himself migrated to the Loire Valley where he spent his final years. He brought the Renaissance with him, leaving a few more gifts of design behind in France bringing with him the influence he lent to the Italian cities he stayed in, including Florence, Milan, Venice and Tuscany. brbrGuest Suites & AccommodationsbrbrEach bedroom is presented as a private suite with en-suite bath, designed for comfort, flexibility, and independence.brbrMain Levelbrbr* Napoli Suite — 2 Double Bunk Beds end to end, for a total of four fulls + office spacebrbr* Tuscany Suite — Expansive King Master Suite, Direct Ocean Views and a 2 tier private balcony to soak in sunlight and sea breezes. brbrUpper Levelbrbr* Milan Suite — Queen Bunkbed Suite Combines Elegance and Decadence, each with a private Televisionbrbr* Venetian Suite — Opposites Attract - This Queen Bunkbed Suite Has Decadence Then Elegance - Both Rooms can connect for a Quad Queen Double Bunker Mega Suitebrbr* Florence Suite — Queen Guest suite, Pristine and Clean Aesthetic designed for you to focus on yours.brbr* Gran Lux Suite — A King Suite Both Grand and Luxurious in scale; Travertine x Zebra Marble Spa Bath screams next in line for the throne.brbr* Palazzo Suite (Master) — Expansive king suite with plush shag carpeting to always greet your feet, Champagne mini bar, chandeliers, columns, Versace adornments, commanding ocean views, and a private terrace of equal scale. A vantage the Palatine would adore.brbrAcross all suites: integrated lighting, refined finishes, and a consistency of design that carries throughout the estatebrbrChâteau on the Ocean represents a total transmutation of space. We have engineered a high-performance environment where the architecture, the social flow, and the raw energy of the elements work in a singular, uninterrupted synergy. Château on the Ocean was engineered for the art of the host—creating a seamless flow from the curated interior to the water’s edge.brbrWe spared no expense with that principle in mind, designing every square foot to facilitate the perfect experience while keeping the horizon in constant view...brbrChâteau on the Ocean — Key Facts & Figuresbrbr* Bedrooms: 7 (7 Suites, All with Private Bathrooms) br* Bathrooms: 10.5br* Overnight Guests: 14br* Living Area: 10,182 sq ft under airbr* Total Built Area: 19,784 sq ftbr* Lot Size: ~80,000 sq ftbr* Ocean Frontage: 120 feet direct Atlantic Ocean frontagebr* Year Built / Renovated: Fully redeveloped & completed 2023br* Property Type: Single-family oceanfront estatebr* Dock: 100-foot private deep-water dockbr* Pool: Resort-style glass-covered mosaic pool + spabr* Rooftop Terrace: 3,000+ sq ft Skyline Terrace with 360° ocean viewsbr* Ballroom: 40’ x 80’ Baccarat-inspired grand ballroom (3,200 sq ft) with 22-ft ceilings, fully soundproofed, multi-usebr* Key Features: Private beach, indoor sports court, gym, putting green, 300” outdoor LED theater, downstairs bar, poker room, multiple fire pitsbr* Architecture: European Transitional French Châteaubr* Access: Gated with private wrought-iron entrancebrbrPrivacy, Security & ParkingbrbrPrivacy, exclusivity and inclusion are the first elements you’ll notice once within the walls of this Southernmost Shangri-La. brbrFully gated property with controlled entrybrPerimeter fencing/walls for privacybrbrParkingbrOn-site capacity for approximately 10–12 vehiclesbrbrEvents brOn-site parking designated for valet use onlybrMust Have Required Permit in Place PriorbrbrFountainsbrbrAn important defining element of French renaissance gardens were the use of waterways in the form of rectangular ponds or straight canals that emphasized the symmetry of the garden`s design.brbrA linear mosaic fountain draws you inward—until it resolves at the open Atlantic. A seamless current. Water leading water.brbrPool & Spa brbr* Resort-style pool and spa — the dramatic visual centerpiece of the estate, visible from nearly every major room and the grand ballroombrbr* Integrated spa/jacuzzibrbr* Entry courtyard fountains transitioning toward pool and oceanbrbr* Pool positioned for direct ocean viewsbrbr* Direct transition from pool to private beach and ocean accessbrbrHistorically, `Water Chateaus` like Chenonceau were built to command the river. brbrChâteau on the Ocean evolves this concept into the modern paradigm. brbrOutdoor Theater (Sea-nema)brbr* 300-inch outdoor LED screen, fully integrated into the estate’s architecturebrbr* Oversized outdoor sofas, dining enclosure, and cabana seating for layered viewing environmentsbrbr* Ideal for film nights, sporting events, private screenings, and large-scale gatheringsbrbr* Perfectly positioned for a true open-air cinematic experience with the Atlantic as the ultimate backdropbrbrThe lines of continuity become as apparent as abundant. brbrKitchen / Great Room / Oceanfront Dining (Open Layout)brbr* Open-concept great room with full ocean exposurebrbr* Italian marble surfaces brbr* Large center island with waterfall-edge Italian porcelain and seatingbrbr* Wine refrigeration and under-counter appliancesbrbr* Italian porcelain flooringbrbr* Floor-to-ceiling glass wall with telescoping door systembrbr* Linear glass-enclosed fireplace integrated into feature wallbrbr* Integrated whole-home audio systembrbr* Long solid wood dining table (seats 12-14)brbr* Suspended French Empire-style crystal chandeliers (Baccarat-inspired)brbr* Designed for group dining and chef service with full visual exposure to the horizonbrbrThis is the Southernmost Shangri-La, where the garden wall finally gives way to the infinitebrbrLiving Areas & Ingredients for Mother Nature’s Alchemy brbrWhether healing, grounding, energizing, or calming, the intentional use of precious stones, noble metals, and global millwork imparts an energy befitting a destination worth traversing the earth to reach. brbr* Earth’s Memory: Blue Onyx, Green Quartzite, and White Marble—forged through millions of years of pressure—carry a palpable, grounding frequency into the heart of the home.brbr* The Sacred Threshold: The 24K gold-framed entryway acts as a literal `Portal.` brbr* Year of the Water Rabbit born into an era of refined fluidity. This spirit is captured in a synergistic West-to-East axis—a literal line of light and water that flows toward the sunrise, every element aligned to pull prosperity and peace into the center of the homebrbrBeach, Dock & Ocean brbrThe New Paradigm at Château on the Ocean:brbrWhile the masters of the Loire Valley used water to frame the house, the contemporary paradigm expands the house into the water. brbr* Direct oceanfront estate on the Atlantic Ocean in Islamorada, Florida Keysbr* Exclusive private beach access — whether its a party of 1 or 100 - you make that distinction and you alonebr* 120 feet of prime ocean frontage with a wide, private white-sand beachbr* Crystal-clear Atlantic waters immediately offshore, renowned for exceptional snorkeling and swimmingbr* 100-foot private dock with direct ocean access - leave Fontainebleau and 90 mins later you’ll be arriving here brbrGrand Ballroom brbrWe looked to the Château de Fontainebleau for the true revolution of the arrival, the iconic Horseshoe Staircase. It is the inspiration for our very double grand staircases, aligned in perfect symmetry. brbr* 40 by 80 feet with 22-foot ceilingsbr* Formal receptionsbr* Private nightclub configurationbr* Basketballbr* Pickleballbr* Fully soundproofedbr* Trellised ceilings support Baccarat-scale chandeliers massive and poised to illuminate at a moment’s noticebrbrAdjacent: a full bar, lounge, and poker roombrbrSkyline Rooftop Terracebrbr* 5,000+ sq ft elevated terrace, positioned ~35 feet above the waterlinebr* Unobstructed 360° ocean views, capturing both Atlantic expanse and Gulf horizonbr* Whether a glass of blush, red or white is your preference, sunset is the perfect time to cheers to the heritage of the Chateau…however, a red may be most appropriate…brbrA super model and actress born Margot Louise Hemingway (yes, the Hemmingway) changed her name to the correct spelling of Margaux. She had recently discovered it was the wine — Chateau Margaux — her parents shared the evening that lead to her very conception. brbrA Hemmingway & Château SynthesisbrbrHer Grandfather Ernest’s favorite place on the planet (he even famously mused it may be heaven as that’s where his dreams always took him) was the Ritz in Paris. brbrHe loved because it represented the ultimate in luxury, warmth, and nostalgia. brbrPlease be our guest brbrYour glass of Marguax is waiting..brbrbrLicense# 26-0051brbrGuests will have access to all the bedrooms and common rooms. Certain features of the home require staff assistance to enjoy.brbrPrivate concierge on-site for any and all needs, fancies, whims and desires.

Chateau On The Ocean - The Southernmost Shangrila

Islamorada, Florida, United States

7

Bed

10

Bath

14

Sleeps

$411.01

BREATHTAKING OCEANFRONT SETTING brbrThis home is positioned in one of the most desirable oceanfront locations in Islamorada. The water is so close, you can hear the waves gently lapping the shoreline from nearly every room in the house.brbr*Direct Atlantic Ocean exposure on two sidesbr*Spectacular sunrise viewsbr*Enjoy coffee or cocktails from your private balcony just off the main floorbr*Feel completely immersed in the natural beauty of the Florida KeysbrbrABOUT THE HOME – Windjammer Floorplan (2 Bedrooms Upstairs)brbrThis thoughtfully designed pet-friendly coastal retreat spans 1,230 sq. ft. and is ideal for travelers seeking both comfort and serenity.brbrMain Floor Features:brbr*Fully equipped gourmet kitchen with stainless steel appliances, quartz countertops, farm sink, custom cabinets, and full dining areabr*Open-concept living room with panoramic ocean viewsbr*Private ocean-view balcony off the main living area – perfect for relaxing outdoors, dining al fresco, or enjoying the ocean breezebr*Convenient full bathroombr*In-unit washer and dryerbrbrSecond Floor Features:brbrTwo private bedrooms upstairs, both designed for comfort and privacybrPrimary bedroom with ocean views and luxury beddingbrSecond bedroom perfect for guests or family membersbrFull upstairs bathroom with resort-style finishesbrbrThis Windjammer model does not include a loft. All sleeping accommodations are located upstairs to create a peaceful, restful environment separate from main floor entertaining.brbrSleeps up to 6 comfortably with the addition of a sleeper sofa in the main living area.brbrFULLY FURNISHED WITH COASTAL STYLE brbrThis home comes fully furnished in a tropical resort-inspired theme. Each home is privately owned and decorated, which means furnishings may vary slightly—but all units meet professional resort standards for comfort and quality. Everything you need is here, including:brbr*Linens & towelsbr*Cookware & dishesbr*Kitchen essentials & small appliancesbr*Comfortable seating & beddingbr*Decor designed to reflect the spirit of the Keysbr*Just bring your suitcase, and the island life begins.brbrRESORT AMENITIES INCLUDEDbrbrAs a guest in this oceanfront rental, you will enjoy full access to an exclusive waterfront resort offering the best of island living:brbrWATER & RELAXATION brbrHeated oceanfront resort style swimming poolbrLounge chairs along the ocean’s edgebrOceanfront boardwalk for sunrise walksbrEasy water access for paddleboarding and kayakingbrbrACTIVITIES & ENTERTAINMENTbrbrClubhouse with social spacesbrOutdoor game lawn & billiardsbrDaily and weekly resort activity schedulebrLive music (seasonal)brCommunity events, game nights, fitness gatheringsbrbrbrWELLNESSbrbr*Fitness centerbr*Yoga and outdoor wellness activities (seasonal)br*Ocean air, peace, and rejuvenation at every turnbrbrISLAMORADA - THE ULTIMATE KEYS EXPERIENCEbrbrLocated in the heart of Islamorada, you are just minutes from:brbrFine dining restaurants featuring fresh local seafoodbrWorld-class fishing charters (offshore, reef, and backcountry)brFounders Park – directly across the street with a beach, pickleball courts, dog park, marina, and walking trailsbrMarine life encounters, snorkeling excursions, sunset cruises, and eco-toursbrArt galleries, boutiques, and the Morada Way Arts DistrictbrFlorida Keys Brewing Co., museums, historical landmarks, and morebrbrIslamorada is truly a playground for outdoor lovers, foodies, and anyone seeking tranquility in a stunning tropical environment.brbrWHY GUESTS LOVE THIS HOMEbrbr*Unmatched oceanfront settingbr*Balcony directly off the main floorbr*Two bedrooms upstairs for privacy and comfortbr*Fully furnished, turn-key livingbr*Full kitchen for cooking meals at homebr*Resort amenities includedbr*Peaceful, private, and secure resort settingbr*Perfect for month-long staysbrbrMINIMUM STAY REQUIREMENTbrbrTo preserve the peaceful residential experience and comply with community guidelines, a 28-night minimum stay is required.brbrThis makes the property ideal for:brbr*Extended vacationsbr*Monthly corporate staysbr*Seasonal/winter escapesbr*Relocation visitsbr*Long-term island lifestyle experiencesbrbrBOOK YOUR STAY - LIVE THE ISLAND LIFE brbrWhether you choose to spend your days relaxing by the pool, fishing offshore, exploring coral reefs, or lounging on your balcony listening to the ocean, this Windjammer home offers the perfect setting to recharge your soul.brbrHomes like this are rare, and availability is limited.brSecure your dates now and start living the vacation lifestyle you’ve always dreamed of.brbrThe Isla Life starts now – and it starts here.brbrMinimum stay: 28 nights. Boat slips may be booked for an additional fee. Disclaimer: Photos represent the general style and quality of our homes. Each unit is individually owned and decorated, so furnishings and décor may vary slightly. All meet resort standards for comfort and cleanliness.

Hotel Resort

Ocean Waves Below Your Balcony Stunning 2BR/2BA! Min 28-Day Reservation Required

Islamorada, Florida, United States

Bed

Bath

Sleeps

$685.33

Get ready to experience an incredible Islamorada vacation at Maison 305, located in the heart of Islamorada, FL. This waterfront gem is your ticket to luxury, comfort, and tranquility all rolled into one unforgettable getaway.brbrThe moment you walk through the doors of Maison 305, you'll be greeted by a perfect blend of modern style and coastal charm. The spacious living area is decked out with elegant furnishings, calming colors, and breathtaking views of the turquoise waters that define the Florida Keys. Kick back on the plush sofas, soak in the natural light pouring through the windows, and let all your worries fade away.brbrMaison 305 couldn't be in a better spot, surrounded by Islamorada's top-notch attractions, from fantastic dining and shopping to outdoor adventures. Dive into the vibrant coral reefs at Alligator Reef, take a boat ride, or simply take a leisurely stroll through the heart of Islamorada and explore all the best local shops! brWhether you're after a romantic escape, a family retreat, or a fun-filled getaway with friends, Maison 305 promises the ultimate blend of luxury, coziness, and peace. Immerse yourself in the enchantment of Islamorada at this sanctuary. Secure your stay now and create memories that will stay with you forever.brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Condo

Charming 3-Bedroom Condo in Islamorada with Stunning Ocean Views and resort-style pool.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$543.91

Amenities: Pool Table, Bicycles, Paddle Boards, Peloton, Yoga Mat br Resort-Style Amenities: Heated Pool, Dockbr ️ All bedrooms feature ensuite bathroomsbr Oceanfront, Gated Peaceful Palms communitybr Prime Islamorada location near dining + marinasbrbr THE SPACEbrbrWelcome to Island Time, an elevated coastal retreat where relaxed Keys living meets thoughtful, upscale design. Located within the gated oceanfront community of Peaceful Palms in Islamorada, this three level, partial ocean view townhome offers a refined coastal escape. While there is no beach shoreline, guests enjoy dock access, a heated waterfront pool, and sweeping ocean views. This vacation rental was created for guests who crave comfort, style, and plenty of room to unwind. From the fully outfitted recreation floor, with a Peloton, paddleboards, bikes, and a pool-table dining setup, to the bright and breezy main living level and three serene ensuite bedrooms. Every detail is designed to help you slow down and settle into Island Time. brbr WHAT YOU'LL LOVEbrbr✔ Professionally designed interiors with upscale coastal charmbr✔ Large partial ocean-view balcony with dining and lounge seatingbr✔ Full recreation level with Peloton, bikes, weights & pool tablebr✔ Two paddle boards includedbr✔ Three bedrooms, each with its own ensuite bathroombr✔ Additional full bathroom on the recreation levelbr✔ Access to heated community pool and boat dockbr✔ Impact windows, central AC, smart TVs, premium beddingbr✔ Located in the exclusive Peaceful Palms community- Note this is an oceanfront community with no beach access. brbrFIRST FLOOR – RECREATION LEVEL & LOUNGE AREAbrDesigned for fun, fitness, and relaxation. The perfect start to Island Time.brIncluded on this level:br• Two adult bicyclesbr• Peloton bikebr• Two paddle boardsbr• Yoga mats + free weightsbr• Mini fridgebr• Lounge area with large sectional + Smart TVbr• Pool table that converts into a dining tablebr• Murphy bed (size double)br• Full bathroom with walk-in showerbrbrSECOND FLOOR – MAIN LIVING AREA: Light-filled, breezy, and beautifully designed.brbrLiving + Balconybrbr• Stylish coastal-designed living roombr• Smart TVbr• Large partial ocean-view balcony with sofa + dining tablebrbrKitchenbrbr• Full-size appliances: refrigerator, oven, microwave, dishwasherbr• Ample counter spacebr• Fully stocked for long or short staysbrbrSecond Floor Bedroombrbr• Queen bed + twin trundlebr• Ensuite bathroom with walk-in showerbr• Smart TvbrbrTHIRD FLOOR – BEDROOM LEVEL: The top level features two beautifully appointed ensuite bedrooms.brbrBedroom 2brbr• King bedbr• Ensuite bathroom with walk-in showerbr• Smart TVbrbrPrimary Suitebrbr• King bedbr• Balcony with partial ocean viewbr• Ensuite bathroom with walk-in shower + double vanitybr• Smart TVbr• Premium linensbr• Spacious closetsbrbr ️ All bedrooms feature the following amenities:brbr✔ Premium beds, pillows, linens, and sheetsbr✔ Smart TVsbr✔ Ample closet spacebr✔ Tile flooring throughoutbrbrSecond Floor Bedroom: Queen-sized bed + twin trundle, ensuite bathroombrThird Floor Bedroom: King-sized bed, ensuite bathroombrThird Floor Primary Bedroom: King-sized bed, ocean views, ensuite bathroombrbr All full ensuite bathrooms are generously stocked with:brbr✔ Shampoo & conditionerbr✔ Body soapbr✔ Fluffy towelsbr✔ Toilet tissuebrbrBathroom 1 (First Floor): Walk-in shower, sink, and toiletbrBathroom 2 (Second Floor – Bedroom 1 Ensuite): Walk-in shower, sink, and toiletbrBathroom 3 (Third Floor – Bedroom 2 Ensuite): Walk-in shower, sink, and toiletbrPrimary Bathroom 4 (Third Floor): Walk-in shower, double vanity sink, and toiletbrbrCONVENIENCEbrbr- Washer + dryer located inside the home.br- Available parking for one small vehicle in the driveway and an additional vehicle outside the gated complex. brbr OUTDOOR PARADISEbrbrAs a guest at Peaceful Palms, enjoy access to:brbr• Heated community pool with lounge chairsbr• Must check availability. Boats up to 24'br• Poolside restroomsbr• Oceanfront seating areas perfect for sunrise watchingbrbrThe community is quiet, beautifully maintained, and captures the essence of Keys waterfront living.brbr⚓ BOAT DOCKAGE INFORMATIONbrbr-Complimentary boat dockage (subject to availability) -Dockage is limited, we recommend reserving dockage upon booking. The dock is not in a protected marina and subject to weather conditions.br-We can accommodate boats up to 24'. Contact us to confirm if the dock can accommodate your boat.br-No trailer storage on-site.br-No boat ramp on-site.brbr ️ NEIGHBORHOOD OVERVIEWbrbrIsland Time is perfectly located to enjoy everything Islamorada has to offer. Restaurants, boutiques, parks, marinas, and attractions are all within minutes.brExplore by paddleboard or kayak, snorkel the reefs, or bike along scenic island paths. Islamorada is known for turquoise waters, world-class fishing, and its warm, relaxed coastal charm.brbrBicycles, paddleboards, and kayaks can be delivered directly to your villa for an additional fee.brbr POINTS OF INTEREST: Distance measured in driving time, non–rush hour:brbr– Islamorada Library Beach Park (7 min): Water access on a mangrove channel with shaded tables & BBQ areas.br– Morada Way Arts & Cultural District (7 min): Galleries, boutiques, and local cuisine with weekly art walk events.br– Theater of the Sea (4 min): Marine shows, exhibits, and swim-with-dolphin experiences.br– Robbie's Marina (12 min): Feed the tarpon, dine waterfront, browse shops, and enjoy boat tours.br– History of Diving Museum (5 min): Fascinating exhibits detailing the history of scuba diving.br– Anne's Beach (15 min): Calm, shallow waters perfect for swimming and family outings.brbrHOUSE RULESbrbrCheck-in: 4:00 PMbrCheck-out: 10:00 AMbrbr*All guests must sign our rental agreement (as required by Florida law).*brbr- Minimum rental age: 25 (photo ID required 72 hours prior)br- Accurate guest count requiredbr- No parties or unauthorized visitorsbr- Quiet hours: 10 PM – 8 AMbrbrSTARTER SUPPLIES:brbrWe provide paper towels, toilet paper, trash bags, detergent, and bathroom amenities to accommodate the home's maximum occupancy for the first three days.brbrSAME-DAY BOOKINGS:brbr- Require prior approvalbr- Government-issued ID requiredbr- Phone number must match reservation accountbr- No same-day bookings accepted after 2 PMbr- Minimum 3 hours' noticebr- Check-in time may be extended for same-day arrivalsbrbrPET POLICY:brNo pets are allowed. brbrRELEASE OF LIABILITY FOR RECREATIONAL EQUIPMENT:brbrGuests agree to use paddle boards and bikes at their own risk. The property management and owners are not liable for any injuries, damages, or losses related to their use. By using these items, guests release the property management and owners from all claims and liabilities.brbrMID-STAY CLEANING REQUIREMENT:brbr- For all extended stays of 30 nights or longer, a mandatory mid-stay cleaning is required every 30 days.br- If your reservation is 60 days, two mid-stay cleanings will be required, and so on.br- This helps keep the home maintained during longer stays and ensures everything stays in great condition.br- Mid-Stay Cleaning Fee: $285 to be paid by guests.br- We'll reach out after booking to schedule the mid-stay cleaning(s) and send the payment link.

Villa

Island Time: Partial Ocean View, Ensuite bedrooms, Free Dockage, Htd Pool

Islamorada, Florida, United States

Bed

4

Bath

8

Sleeps

$278.62

This brand new home is sitting quietly behind a controlled access gate with a private balcony overlooking the Atlantic Ocean. Full two bedroom, two bath floor plan, has an upscale decor package and is fully furnished - with an optional work-from-vacation home set up in bedroom 2.brWhile your experience will be private, you will have full access to all of the Sun Outdoors Islamorada resort amenities and activities. Including, but not limited to, heated pool, clubhouse, outdoor game lawn, billiards, and ocean front tanning chairs and boardwalk. A social calendar for all guests is always available for those that wish to be more social, while fine dining is only a minutes drive in Islamorada.brIslamorada is the fishing capitol of the world, and you will easily find plenty of nice dining locally. Founders park is directly across the street for those that wish to walk over and have a day at the beach, or just play some pickle ball.brbrCheck out the video of our home below:brhttps://youtu.be/vs-ChBQAxzc

Hotel Resort

Brand New Home, Resort Location, Pet Friendly, Oceanview

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$689.48

This stunning pool home is nestled along a private canal with convenient dockage and quick access to the bay! This luxurious getaway is the definition of relaxation and waterfront living, offering an unforgettable vacation experience.brAs you step into this home, you'll be greeted by a spacious and tastefully decorated living area, designed to create a comfortable and inviting atmosphere. The large windows provide breathtaking views of the peaceful mangrove hammocks across the canal, and allows natural light to illuminate the space and creating a serene ambiance throughout the day. You will find 3 bedrooms and 2 bathrooms upstairs all perfectly furnished to meet everyone in your parties desires. br Bring along your friends & family as this home has a private downstairs apartment 1 bedroom, 1 bathroom with a kitchenette. brThe highlight of this home is undoubtedly the private pool, inviting you to take a refreshing dip or soak up the Florida sun on the comfortable lounge chairs by the poolside. brAdditionally, this vacation rental offers convenient amenities such as a barbecue grill, wifi, and a washer and dryer. Furthermore, the home is ideally located near popular attractions, restaurants, and shopping destinations, ensuring that you have easy access to everything you need for a memorable vacation.brExperience the perfect blend of luxury, comfort, and waterfront living as you create lifelong memories in this incredible retreat.brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Canalfront 4-Bedroom Mangrove Sunset in Islamorada with dockage and 2 boat lifts

Islamorada, Florida, United States

Bed

Bath

Sleeps

$455.63

Escape to your own private floating retreat in Islamorada, surrounded by nature and endless starry skies. This off-grid houseboat offers total seclusion—no neighbors, just peace and beauty. Perfect for nature lovers and stargazers. Please note: Guests may arrive on their own vessel or boar rental options are available, dock access is 200 yards from our mooring. Enjoy unmatched tranquility in the heart of the Florida Keys.brMinimum stay 2 nights.brbrThe spacebrOur houseboat is totally self contained. We store rainwater in large tanks. We ask our guest to conserve our water by limiting showers to 5 minutes. Please make sure all spigots are properly closed at all times. House water is for shower use only. (Non-potable) We are equipped with an ‘instant on’ LP gas water heater for your comfort.br5 gallon jugs of spring-water are supplied for consuming and brushing teeth.brElectrical power is supplied by solar panels and a large battery bank. We ask guests to conserve energy, when possible. We have a small, gas, generator which turns ‘on’ automatically when batteries are low. We are equipped with one 12,000 btu a/c in the salon area and one 9000 BTU a/c in the master bedroom. Coffee maker and microwave oven in kitchen.brWe are equipped with a portable gas BBQ grill which may be used on the forward deck or the stern deck (exterior only). No cooking, smoking or live flames within the interior of the houseboat.brbrGuest accessbrAll living quarters are open to our guests. The top sky deck is also open for sun bathing and stargazing. The stern roof where solar panels are installed are off limits. Please take note.brbrOther things to notebrThe forward main entrance door is extremely heavy and robust.brPlease take great care not to let it swing in the freely. On a cool breezy day please use the cord strap fastened to the rail post near the door to loop around the doorknob to hold it in place.

House Boat

Off-Grid Islamorada Stay

Islamorada, Florida, United States

Bed