Vacation Home Rentals By Owner In Islamorada, FL

Showing 100 Of 365 Vacation Rentals

$1353.64

Waterfront, boat dock, private oasis in the heart of Islamorada! Pool & Sunsets!

Islamorada, Florida, United States

The Butterfly House IslamoradabrbrYou don’t want to miss this! Old Florida charm in the heart of Islamorada on a half-acre private oasis. The Butterfly House is a unique waterfront property offering amazing sunsets from your private dock. The house is nestled in a lush, fenced estate next door to the world-famous Lorelei Restaurant. Enjoy your private pool, jacuzzi, tiki bar, dock, basketball court and much more. Perfect for families and comfortably hosts up to 7 guests. Book now to create memories that will last a lifetime.brbrProperty Layout:brbrThe Butterfly House consists of two separate living spaces: the main house and a detached back cottage. This setup works well for families or groups who want shared space along with a bit of privacy.brbrMain House (3 Bedrooms / 2 Full Bathrooms):brbr- Ocean Room (Primary Bedroom): King bed with an ensuite bathroom. This bathroom also connects to the Palm Room and can be locked for privacy if desired.br- Palm Room: Queen bed.br- Coral Room: Two twin beds.brbrBack Cottage:brbrThe detached back cottage includes a queen bed and a private en suite full bathroom. It’s ideal for guests wanting a quieter, more private space while still being part of the group.brbrAll bedrooms are equipped with smart TVs.brbrThe property is designed to be enjoyed both on and off the water:br- Private dock with sunset viewsbr- Fish-cleaning station located directly on the dockbr- Outdoor standard refrigerator/freezerbr- Ice machine located by the tiki barbr- Private pool and jacuzzibr- Tiki bar br- Basketball courtbrbrFully fenced yard on a 0.56 acre lotbrbrFishing is a big part of how the property is set up. Boat dockage is included with your book but draft requirements apply. The largest boat previously docked at the property was approximately 36+ feet. Guests are responsible for confirming compatibility for their vessel.brbrParking & Boats:br- Large driveway with ample parkingbr- One boat and one trailer allowed per bookingbrbrSecurity & Privacy:brbrFor transparency and guest safety, the property is equipped with exterior security cameras that monitor entry points and outdoor areas only. There are no interior cameras, and guest privacy inside the home is fully respected.brbrJust a heads up, our pool service comes twice a week and our landscaping crew once a week. They access the property through the front gate and may arrive within a wide time window without notice. Pool service is usually Monday and Friday, and landscaping is typically Friday or Saturday. It’s the Keys, we’re happy when everyone shows up! If you’re bringing pets, please keep this in mind so they don’t try to slip out when the gate is opened.brbrIf you’re looking for a cozy, charming Keys home with character, space, and true waterfront, the Butterfly House is a special place to slow down, fish, swim, and enjoy island time together.

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$404.26

/ Nightly

Private Vacation Home

3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys

Islamorada, Florida, United States

Nestled at the quiet west end of Islamorada, minutes from the Channel 2 and Channel 5 bridges famed for Tarpon fishing, this delightful recently updated canal-front house with a heated/chilled private pool offers a tranquil escape for guests. There's plenty of space for everyone to unwind in the hammock, hang by the pool, fish on the dock, or take the kayaks out for a morning catch or afternoon sunset. With a downstairs apartment, second living room, and kitchen, this home is perfect for a multi-generational family or two families traveling together. Imagine waking up to the serene surroundings and enjoying a cup of coffee on the screened-in porch. Don't forget to enjoy the afternoon sunset from the front deck. The home is a short walk to Anne's Beach, Caloosa Cove Marina, and two restaurants. Come rent our place for at least 28 days per city ordinance and enjoy all the wonders Islamorada offers. You don't have to actually stay 28 days; our rates are less than most 2-week rentals.

Bed

Bath

Sleeps

Exceptional(1)

$1409.53

/ Nightly

Private Vacation Home

Experience luxury at The Sapodilla House, a stunning 5-bedroom waterfront retreat in Islamorada.

Islamorada, Florida, United States

The Sapodilla House - The Sapodilla House is one of Islamorada's gems. This tropical, sprawling estate has every amenity and then some. Enjoy island living at its finest from the moment you drive through the private gates.brThe spacious main house is beautifully furnished and equipped with everything you will need. Cook island inspired meals in the high-end kitchen and choose to dine in the formal dining area, breakfast nook with garden views or outside under the tiki hut. The main house features three king ensuites, and a kids' room with full-size bunk beds and your own personal mini arcade. Enjoy the company of family and friends in one of the conversation areas or over a game of pool. The detached pool house includes an additional king bedroom and bathroom. brStep outdoors and the lush, tropical landscaping will have you feeling like you're at your own private resort. Outdoor entertainment areas include an expansive outdoor kitchen (including a bonus grilling area with charcoal and smoker grills), crystal-clear swimming pool and spa, a rooftop sundeck and a fully equipped dock. Dockage with water, shore power and a fish cleaning station right at your reach. Paddle boards and kayaks available for your use. brIf booking more than a year in advance current prices may not reflect 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. 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.

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Bath

Sleeps

$521.13

/ Nightly

Private Vacation Home

Discover La Casita White Marlin, a spacious 5-bedroom escape in sunny Islamorada.

Islamorada, Florida, United States

Welcome to this stunningly renovated 5-bedroom, 3-bathroom home situated on a picturesque canal, offering a seamless blend of modern luxury and serene waterfront living. Nestled in a sought-after neighborhood Port Antigua, this property boasts an array of features that cater to both relaxation and entertainment, making it the ideal oasis for families and waterfront enthusiasts alike.brbrAs you approach the home, you'll be immediately captivated by its charming curb appeal and lush landscaping. The exterior has been meticulously updated, showcasing a fresh coat of paint, and contemporary finishes, exuding a sense of timeless elegance.brbrStep inside, and you'll be greeted by a light-filled, open-concept living space that is both inviting and spacious. Large windows strategically placed throughout the house provide breathtaking views of the canal and fill the home with natural light.brbrThe focal point of the backyard is a sparkling private pool, offering a refreshing escape on warm summer days. Alongside the pool, there is a private dock overlooking the canal. This provides direct access to water activities, whether it's boating, kayaking, or fishing, making it an ideal spot for water enthusiasts to indulge in their passions.brbrBeyond the property itself, the neighborhood offers a welcoming sense of community and is conveniently located to various amenities including the popular White Marlin Beach.brbrThis newly renovated 5-bedroom, 3-bathroom home with a pool and dockage on a canal presents a unique opportunity to experience a lifestyle of luxury, comfort, and waterfront living. With its exquisite design, prime location, and unparalleled amenities, this home is a true gem waiting to be discovered. Come and make this piece of paradise your vacation home.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.

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Sleeps

Exceptional(8)

$724.82

/ Nightly

Private Vacation Home

Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A/C and WiFi

Islamorada, Florida, United States

Minimum 28 day stay. brDreaming of a FL Keys vacation where you can boat, fish, dive, snorkel or stay home and swim in your own private heated pool This is it! The charm of this home begins as you approach this upscale property with tropical landscaping and continue through the double entry doors into a dramatic two-story foyer and ascend the open staircase to continue through the lavish interior with wrap around porches and balconies or simply allow the elevator to lift you to these spaces. The main living area is on the second floor which also boasts 3 bedrooms, 2 bathrooms, kitchen with gas stove, dining table and island seating, TV room and screened balcony which overlooks the custom waterfall pool and dock with 100' wide canal. Unwind in the sitting room or watch your favorite shows on the large flat screen TV. There are 4 additional TV's in the property and each of the three bedrooms on the main floor offer a queen sized bed. One has an ensuite bath with a walk-in shower and the other two bedrooms share a full bath with a tub and shower. The 3rd floor is completely devoted to a master suite. Access is by elevator or a spiral staircase from the main living room/kitchen area. The master is quite spacious and has a king sized bed and private sitting room as well as a private balcony overlooking the water and double sinks in the ensuite bath. brThe main floor of the property has a private apartment which can be accessed through the foyer or a private locked entrance from the outside. It is poolside with a complete kitchen, TV room, Dinette and a King sized bed and full bath. This is perfect for your guests who would like a bit more privacy.brThe exterior of the home is truly a tropical playground. The heated swimming pool is a work of art with an attached elevated spa hidden in a curved rock wall featuring a cascading waterfall.The multi-color LED lit pool is ideal for taking a moonlit dip. There is a cabana area off the poolside which boasts a full air conditioned bath with a walk-in shower. Lounge chairs surround the pool and dock for your relaxing pleasure.brThere is 100' of dock with 60' available for guest use. The fish cleaning station is easily accessible with 50 amp electrical service and water. The canal is deep and wide to accommodate your boat and the Bay and Ocean are only minutes away with easy access through the Snake Creek Draw Bridge, the only drawbridge in the Keys. There is a commercial ice maker in the pool side bar and a fish freezer for bait. brThis home captures the entire essence of The Florida Keys with close excellent dining and water fun all at your fingertips! br

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Sleeps

Exceptional(10)

$387.74

/ Nightly

Private Vacation Home

Incredible Bayside Home in the Florida Keys!

Islamorada, Florida, United States

**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.brbrAs soon as you walk into this home you will feel like you just walked into a comfortable, cozy home. With its cool laid-back style and subtle sophistication this house doesn't disappoint. The home is newly painted and new gravel. Also the backyard has been updated with new artificial turf, which allows for more entertaining space or sun bathing. The house is situated on a canal and features 3 bedrooms and 2 bathrooms, family room, kitchen, dining area, outside deck off the 2nd floor. Our home is situated in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the southernmost island in Islamorada, at exactly Mile Marker 74, on the bayside. The home is a 3/3, and can comfortably sleep six, with three bedrooms and 2 bathrooms upstairs and 1 full-bath downstairs. The Master has a queen bed, and a private bath. The second and third bedroom have queen beds, and a separate bath that is shared. If more room is needed, or for families with older children or adult that cant climb stairs, the lower level is an open floor plan where you can find two sets of bunk beds and sofa sleeper and I full bathroom. Also, you can find on the lower level a laundry room and television to connect any of your favorite game consoles (not provided). A full-size refrigerator for water/soft drinks/beer/bait is located on the first level for easy access to the pool deck. On the pool deck you will find an outdoor barbecue area and gorgeous Tiki Hut with a large pool to soak your worries away. Also, a large 65 foot of dock with Electric & Water; and a fish cleaning station This home provides a private homeowners beach with Tiki Huts, chairs and BBQ Grills. This home is close to the best restaurants, and sightseeing that can be offered in the Florida Keys. brbrPeaceful, quiet and relaxing! Just what is needed to take your mind off of business and a great place to spend the winter months in turquoise, warm waters. Fish, read a book, swim, head to Key West, shop, eat, drink, enjoy the Florida Keys. brbrCome stay in this incredible home and create your own memories!brbr*This is a non-smoking unit. Sorry, no pets. No large groups or individuals under the age of 25.brbr***Service Pets Allowed***brbr****Please feel free to reach out for more information****

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Exceptional(20)

$381.95

/ Nightly

Private Vacation Home

POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage

Islamorada, Florida, United States

Your own tropical paradise in Islamorada overlooking the fabulous brFlorida Bay - this family favorite is just 67 miles south of Miami! brFutura Yacht Club is the best in Islamorada vacation rentals. This bris a gated community & this townhouse features 2 bedroom, 2 br1/2 baths and an incredible view of the Florida Bay. It has a brprivate balcony, full kitchen with dining area, living room and brprivate laundry. brIt is located on the marina and only a step out your door away from brthe pool. There is an uninterrupted view of the Florida Bay and brsensational sunsets from this unit. This townhome is in 'bring your brtoothbrush' condition - breverything you need for your vacation comfort has been thought brof. brProtected dockage in the 53 unit marina is available for boats up to br36 feet w/easy ocean access through Snake Creek or Tavernier Creek.brDockage is available for an additional fee of $200/week or $250/week during holiday weeks. Please request when booking and we will adjust your quotebrThere is now a charge for trailer parking and use of boat ramp. brVacation Rental license # 25-0410

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Sleeps

Exceptional(48)

$387.0

/ Nightly

Private Vacation Home

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Islamorada, Florida, United States

Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing getaway, look no further. Relax with the family in this cozy Island retreat. Completely remodeled! Come enjoy the community heated pool and a morning bike run. Enjoy the Florida Keys with your own private backyard and private parking.

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Sleeps

Exceptional(58)

$691.23

/ Nightly

Private Vacation Home

Pristine pool front home w/ocean views Anglers 148

Islamorada, Florida, United States

Summary:brbrWelcome to Angler’s Reef Resort Villas & Marina - a stunning Islamorada vacation destination. This two bedroom, two and a half bath conch house overlooks the resort style swimming pool and is available for weekly and monthly vacation rentals. Our home has ocean views, 2 spacious decks, a full kitchen, and other inspired amenities for your best vacation yet!brbrbrbrThe Space:brbrLush, tropical landscape adorns this property. Find your home away from home in this two bedroom, two and a half bath conch style townhouse overlooking the resort style swimming pool. Our home has ocean views, 2 spacious decks, full kitchen, and other inspired amenities for your best vacation yet. brbrbrbr- 1 KING bed in the master bedroom with flat screen TVbrbr- 1 QUEEN bed and 1 TWIN over QUEEN bunkbed in the guest bedroombrbr- 2 FULL Bathrooms with SHOWERS and blow dryers; brbr- LIVING ROOM with 2 SEPARATE SEATING areas with TV;brbr- DINING AREA for 6: with a table for 4 and 2 counter seatsbrbr- In-unit WASHER/DRYER;brbr- Fully equipped KITCHEN with a ViIKING appliances, KEURIG coffee maker, toaster;brbr- 2 BALCONIES with seating; brbr- All linens, beach and bath towels, bathroom essentials, kitchen utensils, plates, cookware, glasses are provided. brbrYou don’t need to bring a thing! This home is great for a family vacation. There is also a beach and kayaks available. brbrbrbrReserve your stay today!brbrbrbrGuest Access:brbrDock space is available to rent . - please check slip availability prior to booking. *Moored vessels may not exceed a maximum bridge height of 9 Feet, total length of 31 feet, or draft of 3.5 feet.brbrbrbrThis home is great for a family vacation. There is also a beach and kayaks available. Lush, tropical landscape adorns this property. Call us today to reserve your stay.brbrbrbrThe Neighborhood:brbrWelcome to Angler’s Reef Resort Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths wind through this Caribbean fishing village-styled retreat, dotted with 52 cottages inspired by Native Conch and British West Indies themes and adorned with metal roofs and gingerbread trim. More than five hundred feet of oceanfront and mangroves frame 36 protected, deep-water boat docks, perfectly poised for aquatic excursionsbrbr brbrOffshore, three miles south is the famed Alligator Reef while just east lays the only living coral barrier reef in the Continental United States. Islamorada, located in the heart of the Florida Keys also teems with sailfish, tuna and dolphin in the Atlantic Ocean and tarpon and elusive bonefish in Florida Bay, and is known as the “Sport Fishing Capital of the World.”brbrbrbrGetting Around:brbrHaving a vehicle is highly recommended while vacationing in The Keys. Convenient covered parking at your door brbr(parking accommodates two small cars or one large)brbrbrbrOther Things to Note:brbrOffshore, three miles south is the famed Alligator Reef while just east lays the only living coral barrier reef in the Continental United States. Islamorada, located in the heart of the Florida Keys also teems with sailfish, tuna and dolphin in the Atlantic Ocean and tarpon and elusive bonefish in Florida Bay, and is known as the “Sport Fishing Capital of the World.”brbrbrbrInteraction with Guests:brbrI give my guests space but I am available by phone or email when needed. Please do not hesitate to contact me with any questions or concerns. I love my home and want my guests to enjoy The Florida Keys as much as I do. I will graciously give recommendations for local fishing charters, snorkel & diving excursions, eco tours, restaurants, etc.

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Sleeps

$421.88

/ Nightly

Private Vacation Home

Malayan Palm East 1 Bedroom, 1 Bath Garden View

Islamorada, Florida, United States

Poolside,1 Queen Bed,1 Pull OutbrbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.brbrMany of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brbrGuests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.brbrThe Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home. Both Malayan Palm North and Malayan Palm East must be reserved to open connecting door.

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Bath

Sleeps

$599.67

/ Nightly

Private Vacation Home

Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out

Islamorada, Florida, United States

Poolside,1 King Bed, 2 QueenBeds, 1 Pull OutbrbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.brbrMany of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brGuests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

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Bath

Sleeps

$776.25

/ Nightly

Private Vacation Home

Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View

Islamorada, Florida, United States

Partial Ocean View 1 King Bed, 1 Queen Bed, 1 Pull OutbrbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.brbrMany of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brbrGuests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

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Bath

Sleeps

Exceptional(10)

$433.17

/ Nightly

Private Vacation Home

Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada

Islamorada, Florida, United States

80ft Dock and Boat Lift very close to Islamorada Sandbar and Alligator Reef. Great fishing, diving, snorkeling and boating! 400lb Ice Maker on property to fill your coolers. Large home in upscale neighborhood, very quiet private and peaceful. Tropical views of palm trees and ocean from every window and outside decks. Master Suite takes up the whole third floor with veranda.

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Bath

Sleeps

$534.38

/ Nightly

Private Vacation Home

Fish Tail Palm Ocean View 1 Queen Bed, and 1 Pull Out

Islamorada, Florida, United States

Ocean View 1 Queen Bed, and 1 Pull Out.brbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience. Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brGuests enjoy the beautiful Caribbean decor and high, open ceilings. Please note this ground floor unit does have one step up to the main bathroom. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.

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Bath

Sleeps

Exceptional(2)

$581.58

/ Nightly

Private Vacation Home

Malayan Palm North 2 Bedrooms, 1 Bath, Garden View

Islamorada, Florida, United States

Poolside,2 Queen Beds,1 Pull OutbrbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.brbrMany of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brGuests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.brbrThe Malayan Palm has the option of opening a locked interior door, combining the space into a 3 bedroom, 2 bath home. Both Malayan Palm North and Malayan Palm East must be reserved to open connecting door.

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Bath

Sleeps

$595.07

/ Nightly

Private Vacation Home

Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out

Islamorada, Florida, United States

Poolside,1 King Bed, 2 Queen Beds, 1 Pull OutbrbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.brbrMany of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brGuests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

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Bath

Sleeps

$599.67

/ Nightly

Private Vacation Home

Canary Island Palm South 2 Bedrooms, 2 Baths, Poolside

Islamorada, Florida, United States

Poolside,1 King Bed, 2 Queen Beds, 1 Pull OutbrbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.brbrMany of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brGuests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

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Bath

Sleeps

$618.75

/ Nightly

Private Vacation Home

Princess Palm North 2 Bedrooms, 2 Baths Poolside

Islamorada, Florida, United States

Poolside, 1 King Bed, 2 Queen Beds, 1 PulloutbrbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.brbrMany of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brGuests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

Bed

Bath

Sleeps

$659.21

/ Nightly

Private Vacation Home

Coconut Palm South,1 King Bed, 2 Full Beds, 1 Pull Out

Islamorada, Florida, United States

1 King Bed, 2 Full Beds, 1 Pull OutbrbrResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.brbrMany of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.brGuests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.brbrThis home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

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Bath

Sleeps

$478.13

/ Nightly

Private Vacation Home

1 bedroom, 1 bath, full kitchen, 1 queen bed, 1 queen sleeper sofa.

Islamorada, Florida, United States

1 bedroom, 1 bath, full kitchen, 1 queen bed, 1 queen sleeper sofa.brbrWelcome to The Bird of Paradise. This Ocean front home has everything you need for a relaxing getaway. Custom High ceilings create an open, airy feel to this one bedroom, one bathroom home. The Bird of Paradise has a fully appointed kitchen with everything you need to cook up your fresh catch, or, use the Weber gas grill on your front patio. Just steps away from our marina and activity center, where you will find complimentary bikes, paddleboards, kayaks and fishing poles. Enjoy your morning coffee on the patio, in oversized chairs while watching the sun rise over our world-famous dock. The interior is impeccably decorated with fine furnishings from Tommy Bahama, accessories and wall art from Ocean Gardens, all with your comfort in mind. Cable television is located in the living room as well as the bedroom. Wifi and air-conditioning are accessed throughout the home.brbrThe Bird of Paradise is The Caribbean Resort's ADA accessible home. This home is held for use by individuals with disabilities until all other guest rooms have been rented.

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Rent a place that suits your needs

Condo

View 61 Condo

Hotel resort

View 23 Hotel resort

Private vacation home

View 523 Private vacation home

Bed

Bath

Sleeps

$1409.53

/ Nightly

Private vacation home

Experience luxury at The Sapodilla House, a stunning 5-bedroom waterfront retreat in Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1433.51

/ Nightly

Condo

Experience luxury at Coastal Cove Villa, a 4-bedroom retreat in beautiful Islamorada!

Islamorada, Florida, United States

Bed

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Sleeps

$1948.66

/ Nightly

Private vacation home

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

Islamorada, Florida, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Islamorada, FL

$1353.64

$404.26

$1409.53

$521.13

$724.82

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$381.95

$387.0

$691.23

$421.88

$599.67

$776.25

$433.17

$534.38

$581.58

$595.07

$599.67

$618.75

$659.21

$478.13

Rent a place that suits your needs

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