Vacation Rentals By Owner In Islamorada, FL

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.

Stay Beachside: Ground Floor Studio with Gorgeous Ocean Views

Islamorada, Florida, United States

Bed

Bath

Sleeps

$418.53

Welcome to your island retreat! This spacious ground-floor Den Suite offers the perfect blend of relaxation and fun, complete with all the comforts of home in the heart of the Florida Keys.brbrYour Suite Includes:brAn equipped kitchen with a full-sized fridge, stove, coffee maker, toaster, dishes, and silverware is ideal for whipping up a quick meal.brA cozy living room with a sofa bed, dining table, and a balcony to enjoy tropical breezes.brA serene bedroom with a queen bed, an ensuite bathroom, and access to a den featuring a full sleeper sofa, great for extra guests or a quiet reading nook.brA second balcony off the den for even more relaxation.brbrResort Highlights:br Heated pool for a refreshing dip.br Beach access to soak up the sun.brA General Store is available for your convenience.brOn-site marina with charter boats and boat slip rentals for aquatic adventures.brComplimentary Wi-Fi to stay connected.brbrLocal Perks:brExplore nearby attractions with Caloosa's free transportation app, and enjoy free access to Founders Park with your Caloosa KeyCard! This 25-acre gem features sandy beaches, a saltwater swimming area, and plenty of space to relax and play.brPlease note: Guest passes to Founders Park do not include free use of the pool.brbr**This ground-floor unit does not have a view.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.

Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access

Islamorada, Florida, United States

Bed

Bath

Sleeps

$411.8

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.

Island Time Starts Here: Cozy Ground Floor Suite in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$979.86

Located in Islamorada, enjoy what this 3-bedroom villa has to offer. With 2 king beds and 1 queen bed, guests can relax in the enchanting bedrooms. The 3.5 bathrooms are equipped with a shower, bidet, and hair dryer for added convenience. In the extra bonus open room there is a bunk bed and sofa bed for extra sleeping space. Experience an excellent stay with all the great amenities along with the private plunge pool, community pool and private boat dockage. We hope you enjoy what our place and Islamorada has to offer. Lic 26-5008

Villa

Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl

Islamorada, Florida, United States

Bed

Bath

Sleeps

$407.33

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

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

Islamorada, Florida, United States

Bed

Bath

Sleeps

$416.2

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 Caloosas 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.

Barefoot Bliss: Ground Floor Condo with Den & Dual Balconies

Islamorada, Florida, United States

Bed

Bath

Sleeps

$418.53

Immerse yourself in the serenity of island life with this spacious second-floor pool-view suite thoughtfully designed to host up to 6 guests. It has 2 queen beds, a queen sofa sleeper, and 2 full bathrooms, so it's the perfect choice for family vacations.brbrThe bedroom provides exceptional comfort with two queen beds, an ensuite bathroom, and a private balcony, ideal for unwinding while enjoying peaceful views. The living area adds to the charm, offering a cozy queen sofa bed, a compact yet fully equipped kitchen, a dining table for four, a second bathroom, and an additional balcony for an even more relaxing space.brbrAt Caloosa Cove Resort & Marina, you will enjoy many exciting amenities. Lounge by the large heated pool overlooking the ocean or engage in friendly games of Shuffleboard, Pickleball, Tennis, or Basketball. For a quieter retreat, the small library provides a cozy corner for reading. Fire up the BBQ grills to savor a flavorful outdoor meal with loved ones.brbrBoating enthusiasts will appreciate the on-site marina, which offers convenient boat slip rentals for a nominal fee. This makes it easy to embark on a day of exploration or adventure on the water.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.

Double the Views: Florida Keys 1BR with 2 Balconies & Pool Access

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2171.25

License # 204.brbr| ** 3 payment schedule available** | No Pet Charges | No security deposit |brSATURDAY TO SATURDAY ONLY BOOKINGSbrbrEscape to this welcoming house in picturesque Islamorada. This fantastic property boasts 6 bedrooms, including 5 king beds, 4 custom bunks, 2 cribs, a toddler bed, and more. With 6.5 bathrooms offering amenities like a jetted bathtub, this place is perfect for large groups or families. The Master bedroom offers two additional twin beds on the sun porch and a nursery nook with a crib and toddler bed, making a wonderful family suite. brbrThe Last Resort Too is our sister home to the original Last Resort, offering the ability to cater to larger families and groups. Set on over two acres of prime oceanfront land, complete with a heated swimming pool, 200 ft of beach, and a walking/fishing dock. Nestled behind privacy gates, you will feel right at home in this exclusive enclave of Islamorada. *Please note: V-boats do not have clearance for this dock, flat bottom, and pontoons only. * Please check with us for V-Boat accommodations.brbrThis house can book up to two years in advance and is already taking bookings for 2027.brbr** The owner, who has been part of VRBO since 2004, will be managing the home directly from 2026. As an already established listing on VRBO, reviews do not transfer to this new 2026 listing.

Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool

Islamorada, Florida, United States

6

Bed

6

Bath

14

Sleeps

Select Dates for Price

This luxurious 4 bedroom, 3 bathroom house offers exceptional opportunity to experience the Florida keys in style with its flawless blend of coastal elegance and modern comforts. This property promises an unforgettable retreat for relaxation and adventure. Located in Lower Matecumbe key, mile marker 75, in the highly desired community of Port Antigua, this home has private access to one of the most desired beaches in the Florida Keys with its gorgeous white sand, tiki huts, picnic tables, grill and a private boat ramp makes this a great location to get away for a while. brbrThe main floor layout is open and ready for entertaining with its ping pong/pool table and kitchen island seating. There are four bedrooms with plenty of space to spread out. The two upper bedrooms are en suite style with bathrooms which includes the king bedroom and a double bunk beds room - a twin over full and another full over full. The main floor includes two more bedrooms which share a bathroom - a queen bedroom and other room has twin bunk beds with separate twin and trundle. House includes a total of 9 beds and sleeps 11 comfortably!brbrKitchen has been remodeled and updated with gourmet appliances including a wine/beverage cooler, toaster, Keurig coffee maker, and plenty of kitchenware and barware to entertain. Full washer/dryer.brbrOutdoors includes comfortable balcony seating area, BBQ and dock space for your boat. The property features dockage with a 20,000 lb lift for boat enthusiasts with direct access to the bay. Plenty of free parking and space in front for your boat trailer. brFree WIFI internet included with streaming access on all three TVs. brbrTo comply with local laws and HOA requirements, the minimum rental period is one month, and guests must be at least 25 years old to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.br

Port Antigua Retreat on Canal with Boat Lift and Private Beach Access

Islamorada, Florida, United States

Bed

Bath

Sleeps

$692.9

141 LeSerra Lane - Located at mile marker 76, LeSerra Lane is a three-bedroom, two and a half bath oceanfront home that checks all the boxes needed to make your upcoming vacation the best yet! Enjoy your morning coffee watching the sun rise over the Atlantic Ocean. Jump in your boat and head out to some of the best fishing Islamorada has to offer or simply hang out by the private pool with a cocktail in hand and grill up your catch! We dare you to not have a good time at this property! VACATION RENTAL LICENSE: 24-0020 Please note, the pool is heated from Oct 1-April 1.brPer Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease 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.

Relax in this 3BR open water view home with private pool in Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$592.32

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

Bath

Sleeps

$904.68

Front-Row Ocean Views – A Location That Cannot Be ReplicatedbrbrWelcome to Paradise Palms—the crown jewel of the exclusive Peaceful Palms gated community. Perfectly positioned just steps from the water, this newly built three-story home offers sweeping panoramic views and a rare third-floor oceanfront balcony.brbrWake up to sweeping views of the Islamorada Sandbar and Alligator Reef Lighthouse, nature unfolds right outside your door.brbrEvery sunrise and sunset becomes part of your stay.brbrDesigned for Comfort, Style & Connectionbr• 2 Expansive Oceanfront Balconies – Coffee at sunrise, cocktails at sunsetbr• True Oceanview Kitchen – Rare full ocean-view layout, fully stocked with premium appliancesbr• Oceanfront Living Room – 77” 4K OLED TV, designer furnishings, seamless indoor-outdoor feelbr• Curated Interiors – Clean, coastal luxury with thoughtful, high-end finishes throughoutbr• Pet-Free, Pristine Environment – Guarantees the highest standards of cleanlinessbrbr3 Bedrooms | Sleeps Comfortably with Space to Spread Outbr• Primary Oceanfront Suite (3rd Floor) – Tempur-Pedic King, private balcony, workspace, spa-style ensuite with rain showerbr• Second Oceanview Suite (3rd Floor) – Tempur-Pedic King, twin pull-out sofa, spa-style ensuite with ocean viewsbr• Bunk Room (Main Floor) – Full-over-full Tempur-Pedic bunks + trundle—perfect for kids or additional guestsbrbrThe Ultimate Bonus: Entertainment Retreat – A fully air-conditioned lower-level space designed for endless fun:br• 86” 4K Smart TVbr• Gaming systembr• Full-size ping pong tablebr• Lounge area + bonus fridgebr• Board games, books, puzzlesbr• Plus outdoor fun: cornhole + spikeballbrbrDock + Water Access (A Guest Favorite)br• Boat slip for vessels up to 24 ft (18” max draft at low tide, reservation required)br• Water + electricity at dockbr• Complimentary paddleboards + kayakbr• Oceanfront community pool with loungers, umbrellas & restroombrbrWhile onsite trailer parking is not provided, we will be delighted to share nearby accommodations for your convenience.brbrWhy Guests Choose Paradise Palms Again & Againbrbr“The location was the best one on the property. You see the ocean from every balcony and window.”br“The location was perfect, close proximity to fantastic restaurants and plenty of things to do.”br“The kids LOVED the bonus space downstairs to play ping pong and hang out.”br“I want to live in this home forever! THE VIEWS… WOW!”br“Unrivaled oceanfront positioning—you can’t get closer to the water than this!”br“All I can say is WOW! We travel a lot, have stayed in dozens of vacation rentals all over the country as well as internationally. And this is the best place we’ve ever stayed in by far!”br“You can tell so much care went into every detail, and everything felt spotless and welcoming from the moment we walked in.”br“The views from every window were incredible. Everything about this home was comfortable and top-notch.”br“My boys especially loved playing ping-pong in the game room and fishing off the dock in front of the house. They caught fish every day!”br“AMAZING! 6 adults stayed at Paradise Palms for a week and we were not ready to return home! The space is dreamy with stunning views!”br“Gorgeous decor, comfortable, and so spacious! 3 floors of fabulousness! From ping pong battles, corn hole domination, lazing by the poolside, hanging inside and watching football or walking to Starbucks and the marina…… this place did not disappoint!”br“We have stayed in many rentals all over the country and this home is one of the best we've ever stayed in.”brbrGet a true glimpse of living at Paradise Palms, “Paradise Perfection: I have stayed in vacation rentals for decades... and this topped them all. We had an absolute blast and never wanted to leave. The panoramic ocean views were spectacular! The owners have furnished this place with incredible generosity and luxury, both style and comfort. We had 6 guests and plenty of room for everyone - especially loved the extra entertainment room. From the yummy linens, luxurious towels and spotless amenities; every detail was perfection. A private five-star resort experience all to ourselves. The location couldn't be better; a perfect balance of tranquility and convenience. We slept like babies as the location is QUIET and the beds were TEMPUR-PEDIC BLISS! As foodies, we loved being within walking distance of amazing restaurants and activities. We booked again and have referred our friends - this is a rare gem as it is oceanside, spacious, and brand new!”brbrWalkable Location + Local Favoritesbr• Walk to dining, marina, and activitiesbr• 5-minute walk to Starbucksbr• 1 mile to Publixbr• Complimentary Freebee Tesla rides throughout IslamoradabrbrNearby must-do’s:br• Robbie’s Marina (feed the tarpon)br• Theater of the Sea (walkable!)br• Alligator Reef snorkeling & divingbr• Morada Way Arts Districtbr• Founders Park (beach, pool, playgrounds)brbrA Stay That Feels Different – From the unmatched proximity to the water to the thoughtful details throughout the home, Paradise Palms offers a level of experience that goes beyond a typical vacation rental.brbrWe would be honored to host you. Your comfort and satisfaction are our top priorities. Let us help you turn your vacation dreams into reality.brbrVacation Rental License: 26-5235 | DBPR: DWE505412

Closest Oceanfront Home - 3 Stories, Views & Dock - Paradise Palms

Islamorada, Florida, United States

Bed

Bath

Sleeps

$419.94

Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept secret. A mile-long private beach shared only with Port Antigua residents. It's crystal clear waters, Tiki huts, picnic tables, and BBQ will provide all the relaxation you need. Relax in this designer waterfront cul de sac home with 4 bedrooms, 3.5 bathrooms, and 95' of dockage. The home is fully equipped with everything you need from fast WIFI, linens, towels, cooking, large capacity washer/dryer, BBQ, ice chest, etc. Take pleasure in all the amenities this home has to offer with breathtaking sunset views, this home is one you must enjoy for your families vacation. Copy and Paste video on YouTube: https://www.youtube.com/watch v=-HVPkMfAJpgbr

Breezy Beach Waterfront home in Port Antigua

Islamorada, Florida, United States

Bed

Bath

Sleeps

$255.26

Stunning Bay-View Townhome in Executive Bay Club – Newly Renovated!brbrDon't miss out on this rare gem! Perfectly located in the heart of Islamorada, this newly remodeled 3-bedroom, 3-bathroom townhome at Executive Bay Club offers the ideal escape to the Florida Keys. With two king beds and two twin beds, this spacious, bay-view unit comfortably accommodates families or groups, providing a tranquil retreat just steps from the water.brbrRelax and unwind on your private beach balcony while enjoying breathtaking sunsets over the bay – one of the few units in the neighborhood offering such a spectacular view. Whether you're, enjoying a nightly keys sunset, lounging at the private beach, or taking a dip in the pool, every corner of this home invites you to relax and recharge.brbrResort-style amenities include:brbrPrivate beach accessbrFreshwater poolbrTennis/pickleball courtsbrPlaygroundbrEnjoy the convenience of modern amenities, including air conditioning, high-speed WiFi, and an in-unit washer and dryer. The fully renovated interior features bright, stylish decor and all the comforts of home, making it the perfect place to unwind after a day of adventure.brbrSituated in the heart of Islamorada, you're just minutes away from top-rated restaurants, fishing charters, boutique shopping, and island attractions. Whether you're here for a romantic getaway or a family vacation, this townhome offers the perfect blend of luxury, relaxation, and convenience.brbrInstant book your stay today and experience the best of the Florida Keys!

BAY UNIT! 3-bedroom townhome in beautiful Islamorada with full amenities

Islamorada, Florida, United States

3

Bed

3

Bath

6

Sleeps

$279.0

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 a room within a hotel.brbr✦ Your room is 335 sq. ft, equipped with complimentary toiletries, TV.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 $50 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

Florida Keys Tour! Private Beach Access with Marina! Pets Allowed, FREE Parking

Islamorada, Florida, United States

Bed

Bath

Sleeps

$279.0

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 a room within a hotel.brbr✦ Your room is 335 sq. ft, equipped with complimentary toiletries, TV.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 $50 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

Swim with Dolphins in the Florida Keys! FREE Breakfast & Parking, Marina, Pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$279.0

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 a room within a hotel.brbr✦ Your room is 335 sq. ft, equipped with complimentary toiletries, TV.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 $50 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

Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking

Islamorada, Florida, United States

Bed

Bath

Sleeps

$267.79

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 a room within a hotel.brbr✦ Your room is 335 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.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 $50 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

Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental!

Islamorada, Florida, United States

Bed

Bath

2

Sleeps

$267.79

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 a room within a hotel.brbr✦ Your room is 335 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.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 $50 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

Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool

Islamorada, Florida, United States

Bed