Vacation Rentals By Owner In Islamorada, FL

$562.51

Everything You Need For The Perfect Vacation! 3 Convenient Units, FREE Parking!

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 301 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

3

Bed

3

Bath

12

Sleeps

$427.54

/ Nightly

Apartment

Better Choice for your Vacation! 2 Pet-Friendly Units, Free Breakfast, Pool

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 290 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Bed

Bath

Sleeps

$379.16

/ Nightly

Apartment

Make Your Trip More Enjoyable! 2 Convenient Units, Pets Allowed, Onsite Pool

Islamorada, Florida, United States

Each furnished room offers premium bedding and free Wi-Fi. Our pet-friendly private beach resort features a boat ramp and paid parking, heated pool with ocean views, terrace lawn games, daily continental breakfast, complimentary self-parking, bike rentals, kayaks, paddleboards, and outdoor BBQ facilities.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 301 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere 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✦ Outdoor pool is available.brAdditional features:br • Heated poolbrbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $29.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). 2 dogs max w/ no breed restrictions. Tax inclusivebrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Access To Private Boat Ramp will incur additional charge/nightbrbr✦ Front desk: 8 AM to 9 PM

Bed

Bath

Sleeps

$387.16

/ Nightly

Private Vacation Home

5 Star Modern Oceanfront Islamorada Townhome on the Beach!

Islamorada, Florida, United States

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located in Islamorada's Port of Call community. 5 minute walk or bike ride to several of Islamorada's best restaurants!brbr*Only 10 units are nestled on this oceanfront piece of paradise along Millionaire's Row in Plantation Key/Islamorada. brbr*Perfect location in heart of Islamorada, the Sport Fishing Capital of the World! 90 minutes from Miami, 20 minutes from Key Largo, 90 minutes to Key West brbr* 2 Bedrooms and 2 1/2 bathsbrbr*Bedding: King, Full bunks, Twin bunksbrbr*Sleeps up to 5 but max of 4 adults due to bunksbrbr*Modern kitchen with quartz countertops, all the gadgets for a gourmet meal including Keurig AND regular coffee pot, all pots and pans, utensils, Kitchen-Aid appliances, built in ice/water on freezer, Washer/dryerbrbr*3 Flat-Screen TV's, all with HD stations, over 1800 On-Demand Movies, voice control (one in each bedroom plus living area)brbr*All new mattresses and linensbrbr*Beautiful direct Atlantic ocean view from unit with Palm Tree breezes from screened oversized porches brbr*1550 square feet, covered carport with room for two carsbrbr*Wifi throughoutbrbr*Built out California Closetsbrbr*Seamless Glass Enclosed Shower in Master Bath, tub/shower in glass enclosed guest bathbrbr* Experience 360 degree views from the roof top deck and look out at the finest Islamorada sunrise and sunsets! brbr*Black out Draperybrbr*Get ready to feel the sand between your toes!brbr*Unit has its own barbeque grill and picnic table. brbr*Community includes heated pool, chickee hut with common area barbecue grills and an ocean front sandy beach. Dock is newly built after Hurricane Irma and contains 10 boat slips. Fish off the the new dock or use the two ladders to lower yourself in and out of the ocean for snorkeling or a casual swim in the Atlantic Ocean!brbr* Grounds are home to several Peacock families with babies! You may see them strolling around or take a walk just north of the property and you will be sure to find them!brbr*This hidden gem awaits you with sandy beach, Atlantic Ocean, sunrise and sunsets and all the comforts of your own home or five star hotel room.brbrCheck out our other VRBO Vacation Rental, Island Dreamz Bay House, Vrbo 2076205brbrState of Florida DPBR Vacation RentalbrLicense #DWE5404235brbrVillage of Islamorada Vacation RentalbrLicense #VR-25-0241

Bed

Bath

Sleeps

$1074.39

/ Nightly

Villa

Islamorada Florida Bay Villa Plunge Pool, Boat Dock, Amazing Sunset Views

Islamorada, Florida, United States

Villa by the Bay – Your Islamorada Escape for Sunsets, Fishing & Island LivingbrbrBring your heart, your family, and your fishing gear to Villa by the Bay, a charming island retreat tucked inside the quaint gated community of Coral Cove in the heart of Islamorada. With just eight homes in the community, this peaceful getaway offers the perfect blend of privacy, comfort, and easy access to everything that makes the Florida Keys unforgettable.brbrWhether you're planning a world-class fishing adventure, a relaxing family getaway, or a romantic escape, Villa by the Bay is your ideal home base.brbr Breathtaking Bayfront SunsetsbrbrEnd every day the way island life was meant to be enjoyed—watching the sun melt into the bay from the dock area. Gentle ocean breezes and vibrant sunset colors create a relaxing atmosphere you’ll look forward to every evening.brbr A Fisherman’s ParadisebrbrIslamorada is known as the “Sport Fishing Capital of the World,” and Villa by the Bay puts you right where you want to be.brbrDirect ocean accessbrbrPrivate dockage available (upon request and fee)brbrEasy access to deep-sea fishing, backcountry fishing, and sandbarsbrbrPerfect for bringing your own boat or chartering a local guidebrbrSpend the day chasing sailfish, mahi, snapper, or tarpon, then return home to relax by the pool and relive the day’s best catches.brbr Private Heated Saltwater Plunge PoolbrbrAfter a day on the water or exploring the Keys, unwind in your private heated saltwater plunge pool. The soothing waterfalls and tranquil sounds create a relaxing oasis perfect for evening cocktails, family time, or a quiet morning coffee.brbr Community AmenitiesbrbrCoral Cove is a quiet gated enclave designed for peaceful island living. Guests enjoy access to:brbrCommunity swimming poolbrbrCommunity dockbrbrGated privacybrbrBeautiful bay views throughout the propertybrbrWith only eight homes, the atmosphere remains calm, welcoming, and uncrowded.brbr Walk to Islamorada’s Best Restaurants & BarsbrbrOne of the best parts of staying at Villa by the Bay is the central location. Many of Islamorada’s favorite spots are within walking distance.brbrEnjoy fresh seafood, tropical cocktails, and live music at nearby local favorites. Whether you're craving sunset dining, casual tiki bars, or a lively night out, it’s all just steps away.brbrNo long drives—just pure island convenience.brbr Relaxed Island LivingbrbrVilla by the Bay was designed for easy, comfortable stays where you can truly unwind.brbrWake up to warm tropical breezes.brSpend afternoons fishing, boating, snorkeling, or paddleboarding.brReturn home for a refreshing swim in the plunge pool.brThen end the day watching spectacular Florida Keys sunsets over the bay.brbrThis is the laid-back Keys lifestyle people come back for year after year.brbr Thoughtful Guest AmenitiesbrbrTo help you settle in comfortably, we provide initial starter supplies, including:brbrCoffeebrbrPaper towelsbrbrBasic toiletries for each guestbrbrFor longer stays, additional supplies can easily be purchased locally and are the responsibility of the guest.brbr Optional Private DockagebrbrBringing your boat Private dockage may be available upon request for an additional fee. Please inquire ahead of your stay to confirm availability and details. (Up to a 42 ft boat)brbr Why Guests Love This Homebrbr✔ Private heated saltwater plunge pool with waterfallsbr✔ Beautiful sunset views from the dock areabr✔ Gated community with only 8 homesbr✔ Walkable location to restaurants and nightlifebr✔ Community pool and dockbr✔ Optional private dockage for boatersbr✔ Centrally located in Islamoradabr✔ Perfect for fishing trips, couples, or family vacationsbrbr Your Keys Adventure Starts HerebrbrWhether you’re casting lines at sunrise, exploring the turquoise waters of the Keys, or enjoying sunset drinks on the balcony, Villa by the Bay delivers the authentic Islamorada experience.brbrRelax. Fish. Explore. Repeat.brbrReady, set… book your unforgettable stay at Villa by the Bay today!brbrLicense #26-0059

Bed

Bath

Sleeps

$743.27

/ Nightly

Private Vacation Home

Venetian Shores Home -DOCK remodeled 3/3 POOL/Hot Tub! Deep water Dockage

Islamorada, Florida, United States

126 Palermo DrivebrCheck out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, tiki hut and hot tub.brbrCall Jennifer for more information 305-240-0592.brbrCompletely remodeled in 2021, this concrete home has very spacious bedrooms (each with a KING bed), beautifully appointed with all new furniture, new gourmet kitchens and new bathrooms.brbr70’ of Deep Water dockage included in rate. Bring your big boat(s)! Large, deep canals with Drawbridge out to ocean via Snake Creek! Parking for one trailer on lot.brbrTwo Bedrooms and Two full Bathrooms upstairs with large kitchen and open living floor plan. There is also a full sized washer and dryer and large closets. Wonderful screened porch for your morning coffee where you will be sure to see some great wildlife (tarpon rolling, birds and an occasional dolphin or turtle)!brDownstairs (separate) you will find a Large ONE King Bedroom and Full Bathroom with full kitchen and large living room. Walk out the sliders to the pool deck, and amazing view of the canal.brbrOur on site care taker is in a separate apartment (ground level street side) and is there to help with maintaining the property and is a great resource for local fishing spots!brCome enjoy your next vacation in the best neighborhood in the Keys! Close to restaurants, parks/beach, the famous Islamorada Sand Bar and so much more!

Bed

Bath

Sleeps

$331.58

/ Nightly

Private Vacation Home

Renovated Anglers Reef 2BR + Sleeper + Ocean Views, Pool, Marina, Sleeps 8

Islamorada, Florida, United States

Escape to Anglers Reef, Islamorada’s premier gated community where coastal charm meets resort luxury. This fully renovated two-bedroom, two-and-a-half-bath home—one of the largest floorplans in the neighborhood—comfortably sleeps 8 guests.brbrUpstairs, two spacious suites offer private retreats. The primary suite features a king bed with premium linens, private balcony overlooking the Atlantic, and an ensuite bath with walk-in shower and double vanity. The guest suite includes two queen beds and a full bath.brbrOn the main level, the open-concept living area includes a sleeper sofa, remodeled kitchen with KitchenAid appliances, bar seating, dining area, and a smart-TV-equipped lounge.brbrGuests enjoy resort-style amenities—two sandy beaches, a heated pool, private marina, kayaks, and palm-lined walking paths.brbrBook your Anglers Reef getaway today and experience the best of Islamorada’s oceanfront living.

Bed

Bath

Sleeps

$593.17

/ Nightly

Villa

Ocean's Fourteen:Direct Ocean View-Balconies-Dock-Htd Pool

Islamorada, Florida, United States

Partial Ocean view + 2 private balconiesbr Amenities: Game room, pool, dock br Gated Peaceful Palms communitybr Prime Islamorada location near dining + marinasbrbrTHE SPACEbrbrWelcome to Ocean's Fourteen, a refined coastal retreat set within the exclusive and serene oceanfront enclave of Peaceful Palms in Islamorada. One of just fifteen private villas in this gated community, the home pairs modern architecture with relaxed coastal elegance to create an elevated Florida Keys escape.brGuests enjoy access to premium waterfront amenities, including private dockage and a spectacular oceanfront pool, along with picturesque water views woven throughout the community. While there is no beach shoreline, the setting is ideal for boating enthusiasts, sunset seekers, and travelers who appreciate peaceful oceanfront living away from crowded public beaches.Perfectly positioned just minutes from Islamorada's most celebrated restaurants, parks, boutiques, and marinas, Ocean's Fourteen offers a polished yet laid-back atmosphere that captures the very best of the Keys lifestyle — sophisticated, scenic, and effortlessly relaxing.brbrUpon arrival, you'll find an attached private garage with space for one vehicle, plus additional parking for more cars. brbrThe open-concept second-floor living area is designed for effortless relaxation. Floor-to-ceiling impact glass fills the space with natural light while framing serene ocean views. brbrThe kitchen includes full-size appliances, refrigerator, microwave, dishwasher, and oven, counter seating for five, and ample countertop space for easy meal prep. brbrThe dining and living areas flow together seamlessly, leading directly to the covered balcony. With partial ocean views, the balcony is an inviting space for morning coffee, alfresco dinners, or simply enjoying the ocean breeze.brbr♛The Primary Suite (Upper Level)brbrThe Primary Suite serves as a peaceful sanctuary with calming décor, a queen-sized bed with premium bedding, ocean view, and a private ensuite bathroom. Its elevated location ensures quiet mornings and complete relaxation.brbr ️ All bedrooms feature the following amenities:brbr✔ Premium beds, pillows, linens, and sheetsbr✔ Smart TVsbr✔ Ample closet spacebr✔ Tile flooring throughoutbrbrSecond Floor Bedroom 1: 2 Twin-sized bedsbrThird Floor Bedroom 2: Queen-sized bedbrThird Floor Primary Bedroom: Queen-sized bed, ocean views, ensuite bathroombrbr All full bathrooms are generously stocked with:brbr✔ Shampoo & conditionerbr✔ Body soapbr✔ Fluffy towelsbr✔ Toilet tissuebrbr brBathroom 1 (Main Level): Ensuite, walk-in shower, vanity, and toiletbrBathroom 2 (Upper Level): Ensuite, walk-in shower, vanity, and toiletbrBathroom 3 Primary (Upper Level): Ensuite, walk-in shower, double vanity sink, and toiletbrbrCONVENIENCEbrWasher + dryer located on the third floor. brbr GAME ROOM brbrThe converted garage has been transformed into a fully outfitted game room and hangout space—perfect for friendly competition, relaxing after a day on the water, or entertaining the whole group.brbrGame Room Features:br✔ Pool table that converts to a ping pong tablebr✔ Cornhole setbr✔ Large sectional couchbr✔ Smart TVbr✔ Selection of board gamesbr✔ Small bar area with 4 stoolsbr✔ Retro-style refrigeratorbr✔ Paddleboards available for guest usebrbrThis space offers a fun, laid-back atmosphere that complements the home's upscale coastal design while giving guests a dedicated area to unwind, play, and enjoy time together.brbr OUTDOOR PARADISE brbrRelax and unwind with top-tier amenities, including an oceanfront boat dock, a year-round heated community swimming pool, and walking proximity to Islamorada's best restaurants, shops, wildlife encounters, and fishing hotspots. The pool area offers comfortable lounge seating, restrooms, perfect for cooling off or enjoying a peaceful afternoon under the sun. Watch stunning sunrises from the comfort of your private balcony, or the community's oceanfront dock.brbrCOMMON AREASbrHeated pool + lounge chairsbrRestroomsbrOceanfront boat dockbrbr brIMPORTANT THINGS TO NOTEbrbrBoat Dockage Information: br-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.br br NEIGHBORHOOD OVERVIEWbrSituated in one of the most desirable areas of Islamorada, Ocean's Fourteen places you within easy reach of the village's best experiences. From waterfront dining and boutique shopping to local parks and scenic nature paths, everything you need is just minutes away. Guests can explore the islands by paddleboard or kayak, snorkel the nearby reefs, or simply soak in the vibrant coastal atmosphere that makes Islamorada so special.brbrBikes & paddle boards provided. The area is home to excellent walking and biking routes, ideal for sunrise runs, relaxed afternoon rides, or peaceful evening strolls along the water.brbrKnown for its exceptional fishing, turquoise waters, and welcoming small-town feel, Islamorada captures the true spirit of the Keys with its blend of adventure, natural beauty, and island ease.brbr br POINTS OF INTERESTbrbrDistance 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 RULESbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrbr *All guests must sign our rental agreement as mandated by Florida Law.br– Minimum rental age is 25. A valid photo ID must be provided to the company no less than 72 hours before arrival.br– An accurate guest count must be provided.br- Pets not allowed.br– No parties or events. Unauthorized guests on property will result in fees and/or immediate eviction.br– Quiet hours are from 10:00 PM to 8:00 AM.br- No smoking or vaping. If evidence is discovered of either smoking or vaping, the guest will be subject to a fine of up to $1,000brbrStarter SuppliesbrWe provide trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate this home's maximum occupancy for the first three days of your stay.brbrSame-Day BookingsbrSame-day bookings require company approval. Guests must provide information about their group and purpose of stay. If approved, a government-issued ID is required for verification. Your phone number must match the phone number registered on your account, or your reservation cannot be honored.brSame-day reservations will not be accepted after 2:00 PM. All same-day bookings require a minimum of 3 hours before check-in, and check-in may be extended later than 4:00 PM.brbrRelease of Liability for Recreational EquipmentbrGuests agree to use paddle boards 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:br- 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.

3

Bed

3

Bath

6

Sleeps

$723.62

/ Nightly

Private Vacation Home

Luxurious Home Located In Venetian Shores

Islamorada, Florida, United States

PROPERTY NAME: Bellabr109 Valencia Drive Tavernier, FL 33036brbrLOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Venetian ShoresbrbrMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrbrMILE MARKER: 86brbrDESCRIPTION: Luxurious 4-Bedroom Home in Venetian Shore – A True MasterpiecebrStep into your dream home in the highly sought-after Venetian Shore neighborhood! This stunning 4-bedroom, 5.5-bath residence offers a perfect blend of sophistication, comfort, and entertainment – making it ideal for family living and hosting guests.brKey Features:brChef's Kitchen: Equipped with top-of-the-line appliances from Wolf, Sub Zero, Bosch, and more. Whether you're preparing a casual meal or hosting a dinner party, this kitchen will inspire your culinary creativity.brEntertainment Paradise: Enjoy hours of fun in the Game Room, complete with a pool table, foosball, and classic arcade machines including Miss PacMan, Frogger, and Donkey Kong. For even more excitement, try your luck with the slot machine, or unwind at the full bar with plenty of seating.brPrivate Office & Spacious Layout: Work in peace in the dedicated Private Office, and take advantage of the expansive living areas that create a warm and inviting atmosphere.brMaster Suite Retreat: The Primary Bedroom offers the perfect sanctuary, featuring an en-suite bath with a claw-footed tub, separate toilet room, full shower, and dual vanity for a spa-like experience.brGuest Rooms & Bath: Two spacious Guest Rooms connected by a Jack & Jill bathroom ensure comfort and convenience for family and guests.brUpstairs on 3rd Level you have the Ultimate Mans cave, Two Tv's , Sofa, Bar Area with Mini Refrigerator and Ice Maker for enjoying cocktails while watching your favorite sportsbrRoof Top Sun Deck for sunbathing or enjoying the beautiful stars at nightbrOutdoor Paradise: Relax or entertain in the open and spacious pool area, featuring a heated pool with a built-in seating shelf for ultimate comfort.brOutside Full Bathroom located next to the Pool areabrUnmatched Comfort & Style: Every room is beautifully furnished with top-tier pieces, creating an atmosphere of both luxury and warmth.brDeep water for the bigger boats with no fixed bridges to the OceanbrOnly a short boat ride to the Famous Sand BarbrbrSleeping Arrangements: Sleeps 9 comfortablybrPrimary Bedroom: King, with ensuite bath with Tub, Shower, Dual sinks and a separate toilet roombrGuest Rooms upstairs, both have Queen beds with a Jack and Jill Bathroom brGuest Room downstairs, Queen bedbr3rd Level has a pull out single couch for sleepingbrbrAmenities Include: Heated Inground Pool, Dockage for boats up to 30 ft 2nd floor balcony for outside entertaining just off Kitchen. brActivities: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures.brbrENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family.

Bed

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Sleeps

$407.33

/ Nightly

Private Vacation Home

Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!

Islamorada, Florida, United States

Discover the Keys from a unique perspective at this Islamorada rental home, a true haven for fishing enthusiasts! Positioned near the island's end, this residence offers secure dockage and immediate access to the Florida Bay and Atlantic Ocean – a fisherman's paradise with some of the best tarpon fishing in the world.brbrAfter a day of outdoor adventures, relax in this well-appointed home with various views. The third floor houses the master suite with its own balcony, providing an intimate spot for sunset views and an ideal vantage point for planning your next fishing expedition. Mullet are always around, offering fresh bait for your angling pursuits right from the premises.brbrThe main level features an open layout with a living room, gourmet kitchen, and a generously sized bedroom and bath. The lower level boasts three more bedrooms, a bathroom, and a living area accessed by an interior spiral staircase – perfect for solitude or communal enjoyment after a successful day on the water.brbrExplore nearby trailer storage options for your convenience. With a two-vehicle limit on the property, your boat trailer can be stored off-site. The dock accommodates vessels up to 34 feet, and the boat lift handles boats up to 26 feet – ensuring you're well-equipped for an extraordinary fishing experience.brbrA sandy beach on the premises is perfect for easy paddleboard launches or simply unwinding. Plus, relish the chance to witness dolphins frolicking in the nearby waters directly from the porch, adding an extra touch of magic to your island getaway.brbrImmerse yourself in Islamorada's charm at this retreat, where every detail invites you to experience the perfect blend of adventure, relaxation, and unparalleled fishing opportunities. br

Bed

Bath

Sleeps

$484.11

/ Nightly

Private Vacation Home

New saltwater pool, pet friendly, waterfront house with dock

Islamorada, Florida, United States

Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of parking. Outdoor shower and BBQ. Upstairs has 2 bedrooms (1 with a king and 1 with 2 queens), a hallway full bathroom, living room, kitchen combo with stove, dishwasher, and fridge, W/D. Downstairs has a mother-in-law suite with 1 queen bed and a queen sofa pullout with own kitchen, stove, and fridge. Full bathroom in the suite. Ramp at Sea Bird Marina for a fee.brbrPayment with credit card thru the VRBO website only. Any other request is a SCAMMER.br

Bed

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Sleeps

$416.2

/ Nightly

Condo

Anchor Here: Oceanfront 1BR Condo with Marina Access

Islamorada, Florida, United States

Immerse yourself in the tranquility of island living with this spacious first-floor pool-view suite, perfectly designed to accommodate up to 6 guests. Featuring 2 queen beds, a queen sofa sleeper, and 2 full bathrooms, this suite is an excellent choice for a memorable family getaway.brbrThe bedroom offers ultimate relaxation with two queen beds, an ensuite bathroom, and a private balcony, perfect for unwinding while soaking in the peaceful surroundings. brbrThe living area enhances the experience with a queen sofa bed, a compact yet fully equipped kitchen, a dining table for four, a second bathroom, and an additional balcony for extra space to enjoy the view.brbrAt Caloosa Cove Resort & Marina, guests can indulge in a variety of amenities. brRelax by the large heated pool with stunning ocean views, or enjoy friendly matches of Shuffleboard, Pickleball, Tennis, or Basketball. brbrFor a quieter escape, the small library provides a peaceful reading spot. Savor a delightful outdoor meal using the BBQ grills, perfect for family gatherings.brbrFor those eager to explore the water, the onsite marina offers boat slip rentals for a nominal fee, making it easy to set sail for a day of fishing or adventure on the crystal-clear waters of Islamorada.brbrThis suite blends comfort, leisure, and adventure, ensuring everything you need for a truly unforgettable island retreat!

Bed

Bath

Sleeps

$418.53

/ Nightly

Condo

Barefoot Bliss: Ground Floor Condo with Den & Dual Balconies

Islamorada, Florida, United States

This spacious suite offers comfort and convenience and is located on the ground floor with a pool and partial ocean views. The well-appointed kitchen features a full-sized fridge, stove, coffee maker, toaster, and all the essential dishes and silverware, making it easy to prepare meals. The inviting living room is furnished with a sofa bed and dining table, while the balcony lets you enjoy refreshing tropical breezes. A convenient bathroom completes the main living area.brbrThe tranquil bedroom offers a queen bed and access to a cozy den with a full-sized sleeper sofa, ideal for additional guests or a quiet reading nook. The bedroom also includes an ensuite bath, and the den opens onto a second balcony for more relaxation.brbrCaloosa Cove Resort and Marina boasts many amenities, including a heated pool, beach access, a General Store, and complimentary Wi-Fi. For those seeking adventure, the on-site marina offers Charter Boats and boat slip rentals for a nominal fee, making diving into world-class sport fishing and other aquatic activities easy.brbrGetting around is effortless with Caloosa's free transportation app, and the Caloosa KeyCard provides free access to Founders Park, a 25-acre paradise featuring sandy beaches, a saltwater swimming area, and ample space to unwind and explore.brPlease 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.

Bed

Bath

Sleeps

$326.3

/ Nightly

Condo

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

Islamorada, Florida, United States

Experience the beauty of Islamorada in this spacious ground-floor studio designed to accommodate up to three guests. With stunning ocean views and cozy comforts, your tropical retreat awaits.brbrSuite Features:brQueen-Size Bed: Sink into comfort each night after a day of exploring or relaxing.brTwin Sleeper Sofa: Ideal for an additional guest or to curl up with a good book.brPrivate Patio: Step outside to enjoy the ocean breeze, vibrant sunsets, or your morning coffee surrounded by stunning views.brCompact Kitchenette: Prepare light meals with ease using the full-sized fridge, stove, and coffee maker. Dishes and silverware are provided, though there is no dishwasherbrbrResort Amenities:brAt Caloosa Cove Resort and Marina, we’re here to make your stay unforgettable:brbrHeated Pool: Lounge poolside or take a refreshing dip in our inviting heated pool.brBeach Access: Stroll along the soft sands or bask in the sun on our peaceful stretch of beach.brGeneral Store: Stock up on snacks, drinks, and vacation essentials.brFree Wi-Fi: Stay connected with complimentary high-speed internet throughout the resort.brCharter Boats and Marina: Dive into adventure with fishing charters or rent a boat to explore the turquoise waters.brDiscover Islamorada:brKnown as the Village of Islands, Islamorada is a paradise for relaxation and adventure:brWorld-Class Fishing: Experience why Islamorada is the Sport Fishing Capital of the World.brLocal Charm: Explore unique shops, mouthwatering restaurants, and local attractions.brFounders Park Access: Enjoy free entry to this 25-acre haven featuring sandy beaches, a saltwater swimming area, and plenty of space to unwind, courtesy of the Caloosa KeyCard.brPlease 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.

Bed

Bath

Sleeps

$413.98

/ Nightly

Condo

Tropical Tranquility: Oceanview 1BR Suite on the Island

Islamorada, Florida, United States

Embrace the tranquility of island living in this spacious second-floor ocean-view suite, designed to accommodate up to 6 guests. With 2 queen beds, a queen sofa sleeper, and 2 full bathrooms, this suite is perfect for family getaways. brbrThe bedroom offers ultimate comfort with two queen-sized beds, an ensuite bathroom, and a private balcony where you can unwind while taking in the serene views. In the living area, enjoy a cozy queen sofa bed, a compact yet fully equipped kitchen, a dining table for four, a second bathroom, and an additional balcony for even more scenic views.brbrAt Caloosa Cove Resort & Marina, you will have access to a variety of fun amenities. Relax by the large heated pool with breathtaking ocean views, or enjoy friendly competition with Shuffleboard, Pickleball, Tennis, and Basketball. For those looking for a quiet escape, the small library is perfect for a peaceful read. BBQ grills are available for a delicious outdoor meal.brbrThe onsite marina offers boat slip rentals for aquatic enthusiasts for a nominal fee, making it easy to take your boat out for a day of adventure.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.

Bed

Bath

Sleeps

$1077.98

/ Nightly

Private Vacation Home

Islamorada Paradise on Snake Creek

Islamorada, Florida, United States

Located directly on the water in fabulous Venetian Shores, Islamorada’s premier community. Our luxurious 5 bedroom/ 5.5 bath home in Venetian shores overlooking the blue waters of Snake Creek and the Islamorada wildlife sanctuary, has everything you need for your Florida Keys vacation. This home is only minutes from the best fishing in the world with no fixed bridge for access. You will find peace and privacy as the tide rolls in and out with nothing but mangroves behind you. brbrMake a gourmet meal near the pool in the outdoor kitchen or relax on the screened balcony just off the dining room or have a family movie night with any of the ultra hi-definition televisions. Cable, Wi-Fi and high speed internet are included. Retire to the master suite and watch the world famous sunset over the mangroves all from the comfort of the private rooftop area. Then enjoy a steam in the custom steam shower or the comfort of your king size Sleep Number bed. brbrYou’re here to enjoy the great outdoors. Enjoy a dip in the heated pool or hot tub. Show off your skills at the gourmet outdoor kitchen with gas appliances and a Kamado Joe charcoal grill for that die hard BBQ expert! Worried about no see ums or Mosquitoes interrupting your time Not here. With the mosquito net, tiki torches lit, and fire pit, they won’t dare to say “hi. If they do, push the mosquito net button and you’ll be able to enjoy the outdoors which is the purpose of your trip!brbrAfter a day of fishing or on the water, relax in the pool while food is cooked on the grill or the kamoda Joe while watching the game on the TV.brbrRelax and enjoy watching the wildlife, and feeding the resident snapper and tarpon behind the house after the sun goes down. If your lucky, you may meet the manatee or pods of dolphin that swim by from time to time. Dock your boat on our 55 feet of dock. Please feel free to use the 650-pound ice machine conveniently located just inside the garage. There are several two-person kayaks for you to explore with. We welcome you to experience our home and make memories that will last a lifetime!!!

7

Bed

4

Bath

10

Sleeps

$397.1

/ Nightly

Private Vacation Home

Casa Del Pirata / 3 bed / 2 ba Canal Home in Islamorada

Islamorada, Florida, United States

Welcome to Casa Del Pirata! brbrLocated in the heart of Port Antigua, this canal front home boasts tropical vibes and can accommodate up to 6 guests to experience the “island life style.” Inside you will find an open living space permitting endless entertaining, a fully stocked kitchen with everything you need for home cooked meals, dining area for four, living room with an oversized sectional sofa, smart TV with cable and wifi, laundry room with a full-size washer/dryer, three bedrooms (one king, two queens) and two full bathrooms. brbrStep outside to the large screened-in back porch and sip your morning coffee while watching the boats go by, or grill your catch of the day while the sun sets and lights up the sky in hues of orange, pink and purple. Biscayne Blvd is one of the few streets that backs up against our protected mangroves and provides extra privacy that other canal front homes can’t offer. The spacious downstairs area offers a covered outdoor space that can be used for dining, relaxing or escaping the Florida sun. brbrBring your boat, kayaks or paddle boards and take advantage of the 75’ of private dockage and 12,000 lb boat lift. Casa Del Pirata is only four houses in from the Florida Bay and just a short boat ride to Channel 5 bridge for easy oceanside access. brbrPort Antigua is a highly sought after community in Islamorada as it is known for its wide canals, boat ramp, and infamous bay front white sandy beach with tiki huts and picnic tables. These are private amenities and are only accessible by Port Antigua homeowners and guests. brbrThis home is located on the island of Lower Matecumbe Key. Just 5 minutes north is the world famous Robbies, which offers fishing and snorkel charters, a restaurant and bar, shops, parasailing, kayaks and paddle board rentals. You can even hand feed the enormous tarpon! Habanos is another local favorite, where you can experience oceanfront dining and classic cuban cuisine. Downtown Islamorada is only 10 minutes north and offers endless restaurants, breweries, shopping, activities and grocery store. Key West is a beautiful 1.5 hour drive south.brbrThis could be just the getaway you need, for more information contact us at (305) 664-0077.brbrHave any questions Feel free to ask away! Coastal Vacation Rentals of the Florida Keys is located in the heart of Islamorada and has a full office staff to ensure you have the best vacation possible.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. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one of our associates to confirm pricing and availability.

Bed

Bath

Sleeps

$418.53

/ Nightly

Condo

Island Time Starts Here: Cozy Ground Floor Suite in Islamorada

Islamorada, Florida, United States

Start your day with coffee on your private patio, soaking in the fresh sea breeze as you plan your Florida Keys adventures. Relaxation is always within reach, whether you are basking on the private beach or enjoying a dip in the heated pool. For thrill-seekers, water activities and boat charters are just steps away.brbrThis spacious one-bedroom, two-bathroom suite features an equipped kitchen (no dishwasher), two queen beds, and a queen sleeper sofa. The open living area, with light wood tones, creates a calming retreat for up to six guests.brbrAt Caloosa Cove Resort, enjoy a heated swimming pool, beach access, and a General Store for your essentials. Our marina offers boat slip rentals for an additional fee, making it easy to explore the sparkling waters of Islamorada.brbrNote: This ground-floor unit does not include ocean views. Thank you for your understanding.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.

Bed

Bath

Sleeps

$331.83

/ Nightly

Condo

Second Floor Ocean View Studio – Gorgeous Waterfront Escape

Islamorada, Florida, United States

Experience the beauty of Islamorada in this spacious second-floor studio, thoughtfully designed to accommodate up to three guests. With breathtaking ocean views and all the comforts you need, your tropical retreat awaits.brbrSuite FeaturesbrQueen-Size Bed: Relax and recharge on a cozy queen bed, perfect after a day of adventure or lounging by the sea.brTwin Sleeper Sofa: Ideal for an additional guest or a cozy spot to unwind with a book.brPrivate Balcony: Step outside to take in the ocean breeze, vibrant sunsets, or your morning coffee amidst stunning views.brCompact Kitchenette: Easily prepare snacks or light meals with a full-sized fridge, stove, and coffee maker. Dishes and silverware are provided, but please note there is no dishwasher.br brResort AmenitiesbrAt Caloosa Cove Resort and Marina, you will find everything you need for a relaxing and unforgettable stay:brbrHeated Pool: Cool off or soak up the sun in our inviting, heated swimming pool.brBeach Access: Enjoy a peaceful stretch of sand perfect for sunbathing or leisurely strolls.brGeneral Store: Conveniently stock up on snacks, beverages, and essentials.brFree Wi-Fi: Stay connected with complimentary high-speed internet.brCharter Boats and Marina: Get adventurous with fishing charters or boat rentals to explore the pristine turquoise waters.brDiscover IslamoradabrKnown as the Village of Islands, Islamorada offers the perfect blend of relaxation and excitement:brbrWorld-Class Fishing: Discover why Islamorada is celebrated as the Sport Fishing Capital of the World.brLocal Charm: Explore one-of-a-kind shops, delicious restaurants, and unique attractions.brFounders Park Access: The Caloosa KeyCard provides free entry to this 25-acre paradise with sandy beaches, a saltwater swimming area, and plenty of space to relax and play.brPlease Note: Guest passes to Founders Park does not include use of the pool.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.

Bed

Bath

Sleeps

$418.53

/ Nightly

Condo

Stay Salty: Keys Dreams 1BR Condo Steps from the Sand

Islamorada, Florida, United States

Discover the spacious comfort of our 1-bedroom, 2-bathroom suite, offering a tranquil haven for guests to unwind. Relax in the bedroom with two queen beds, an ensuite bathroom, and a private balcony for a peaceful retreat. The living area exudes warmth and hospitality, featuring a cozy queen sofa bed, a compact yet functional kitchen with a dining table for four, a second bathroom, and an additional balcony. While our property boasts an oceanfront location, please note that this unit does not have a water view. brbrAt Caloosa Cove Resort, guests are treated to breathtaking vistas, a welcoming heated swimming pool, a serene beachfront, a convenient General Store, boat slips, and exciting boat charters. With an abundance of activities just moments away, it's the perfect destination to unwind and fully immerse yourself in the enchanting ambiance of Islamorada.

1

Bed

2

Bath

6

Sleeps

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