Vacation Condo Rentals By Owner In Islamorada, FL

Oceanside 3/3 located in a beautiful naturally protected harbor on the Atlantic Ocean. See manatee, tarpon and many beautiful species of bird and fish in this amazing natural preserve, Enjoy a scenic sunset over the harbor or ocean views while relaxing in the 2nd floor living room. Enjoy new furnishings, bedding, electronics, appliances & more. Soak and relax in a new heated swimming pool with an 8 person hot tub. A true gem of the Florida Keys with resort style amenities and privacy of private island. This home is kept fresh and meticulously maintained. Monthly or 28 day minimum calendar bookings only. Outdoor ring cameras in front and back of property for safety and security purposes only.

Beautiful Harbor Front Oceanside Home on the Atlantic Ocean

Islamorada, Florida, United States

Bed

Bath

Sleeps

$609.83

Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenient access either bay or ocean with protected dockage. This canal front home has 2 king en-suites upstairs and a relaxing screen porch off of the living room. There is a downstairs apartment with 2 bedrooms and 1 bathroom and small kitchen area. The pool is situated canal side and perfect after a long day of boating. Enjoy grilling your catch in your outdoor canal side kitchen. There is a 28 day minimum requirement on this home…please do not request or ask for altered time as it will not be accepted.

Venetian Shores Pool Home

Islamorada, Florida, United States

Bed

Bath

Sleeps

$2119.45

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

Bed

Bath

14

Sleeps

$515.95

**HOUSE HAS BEEN RENOVATED AND PICTURES TO COME**brPerfect Vacation Home in Islamorada, the center of the Keys Island. The house is ideal for a large family get away, or a small intimate escape. It is perfectly situated between canals providing guests with an unforgettable keys breeze. You are conveniently located near supermarkets, restaurants, and fun activities, like Theatre of the Sea. Take a walk to the community private beach which is only accessible through key access. The house is equipped with 75 total dock space with approximately 35 feet of that dock space to accommodate your boat. It has been updated with a new pool and resort style yard for your enjoyment. Beautiful open views and quick access to ocean. The house is located in one of the most well known fishing areas, Islamorada, renowned for the best fishing areas.brbr

Feel the breeze of the keys

Islamorada, Florida, United States

Bed

Bath

Sleeps

$407.81

If you are looking for peace and tranquility or somewhere to launch and dock your boat for the best fishing and diving in the heart of Islamorada look no further!brbrThe Nest is one of seven villas nestled on a private one acre tropical hammock directly on Florida Bay with stunning water and sunset views. It is close to everything that beautiful Islamorada has to offer and is located only a 90 minute drive from Miami International Airport (MIA) and 2 hours from Fort Lauderdale (FLL).brbrThe property is located directly on the water and it is an easy walk to numerous shops, bars and great restaurants. The villa is private and secluded, away from traffic yet is convenient to many of the best attractions in the upper on Keys. brbrThe villa consists of a spacious Master Bedroom (King Bed) with en-suite bathroom, a living room / dinning area, an open plan fully equipped kitchen with a pull-down (Queen) Murphy bed annexed to the living room (with its own private bathroom).brbrOpen the front door to a large private roof-top terrace with sun loungers, umbrellas, relaxing seating and outside dinning table & chairs. A gas barbecue is provided for you to grill your fresh catch! brbrA Boat launch ramp, sheltered marina (for boats up to 26 ft.) and on-site boat trailer parking are included with the rental. brbrThe villa is air conditioned and there are ceiling fans throughout. The kitchen is fully equipped with oven, range, toaster oven, microwave, dishwasher, Fridge- Freezer (with ice-maker), coffee makers (Keurig & Drip), dishes, pots & pans. Plate-ware and utensils for 6+ persons.brbrBed linens, towels (including beach towels) bathrobes, soaps & lotions are provided.brbrThe living room and dining area (with an expandable table for 4) is bright and sunny with great water views through the large picture windows. The entertainment center has a Flat screen TV and Bluetooth speaker. brbrA full size stacked washer / dryer is provided in the second bathroom along with an iron and ironing board.brbrA boat ramp is available for launching boats up to 18-20 ft. and the marina can accommodate boats up to 26 ft. (larger boats will need to launch elsewhere). Free on-site trailer parking is available. The marina is sheltered and secure with dockside electric, water and lighting.brbrThe property is a nature lovers dream with many resident fish, lobster, octopus and an occasional manatee in the marina. Iguanas sun themselves by the boat basin and pelicans, egrets and osprey fly in for periodic visits. brbrFounders Park is just a short drive north to Plantation Key and well worth a visit, here you will find an Olympic size pool, tennis, pickle ball, soccer, ball fields, dog park, sandy beach and other amenities.brbrYou are minutes away from the best back country (bonefish, tarpon, permit, snook, redfish), blue water (sailfish, mahi-mahi, wahoo, cobia) and reef fishing (grouper, snapper, yellowtail) in the entire Florida Keys. Fishing off of our jetty in the evening is a lot of fun. Magnificent snorkeling and scuba diving sites abound in the local area. A wide range of boating activities are available year round since our area of the bay is well protected.brbrKayaking, canoeing & Standup Paddle Boarding (with a rental store at the end of our driveway) along our shoreline is popular. Of course tubing and knee-boarding are a hit with the kids. Local shopping for clothing, souvenirs, fishing and boating needs is plentiful. Publix Grocery store is close and convenient.brbrThere are a number of local attractions if you need a day out of the sun and Key West is only a day-trip away.brbrThe Nest is a truly unique place, and the people who visit, both owners and guests, feel very special about the property. The privacy is wonderful, the accommodations are fresh and clean, the property is peaceful and the access to the fishing is the best in the Keys. We hope you will also find it as special as have we, and will add your name to the growing list who return to enjoy the most gorgeous sunsets and the best fishing and diving in the world!brbrThe Nest typically rents weekly (Saturday to Saturday) & longer stays are welcome, shorter term rentals are available in the low season. If peace and serenity with great access to the water is what you are looking for, please contact us to reserve your dates! brbrHere's some reviews from past guests....brbrAn Islamorada hideawaybrWe have visited the Nest for over 10 years now! It is a beautiful place, both the living space and the property overall. The owners work to keep the apartment/condo updated with nice furnishings and appliances. The view is wonderful, both the living area and the master bedroom have water views of the lovely Florida Bay. We like to cook while there and the kitchen has everything you need. Together with the gas grill on the deck we have enjoyed great meals. As others have mentioned, there are wonderful restaurants within walking distance or a short drive, we love the walk to the Lorelei for outside dining, views, and music! The jetty at the boat basin is built up on a coral base, has a couple of palm trees for shade, and a fantastic place to sit and read, watch the boats go by, and see the most amazing sunsets. We have loved having our boat with us the past couple of years, just to hop in and explore the area along with great fishing. Key West is about an hour and a half away on a cool sightseeing drive if you are so inclined to become Key Wasted, but at the Nest we usually become afflicted with Keys Disease, which is not wanting to drive more than 5 miles in any direction, it is all right there for you!!brKathy and G. Reidsville, NC March 2022brbrFun Times in the KeysbrThe Nest is in a great location on the bay side , spectacular sun set view. The villa is well cared for and has all the features of home. My wife and I enjoyed our stay immensely. Great place to moor a boat and only steps from your door (included in the condo rental). I rented a boat and fished in the bay. Tarpon fishing was outstanding!!!!! Chilled on the pier in the early evening with the other guest sharing fishing stories and a cold beverage or two. Don is the best, communication is fast and easy. Don looks out for is guest. We are returning in two weeks for you second stay at the Nest!brChuck S. Greenwood South Carolina June 2021 brbrThe Nest, the perfect Florida Keys vacation rentalbrPerfect Florida Keys rental… every time I’ve had the pleasure of enjoying this property it’s been everything I could possibly expect. Clean, lovely and comfortable furnishings, fully, and I mean fully equipped, steps from the water and those spectacular Florida sunsets with the very best view available from the expansive deck or the convenient jetty… you pick! I don’t think there’s a better view available. Great restaurants and bars in easy proximity if you don’t feel like whipping up a meal in the condo or grilling a fish, or 10, on the deck. The owner, is exceptionally responsive and will bend over backward to ensure you have the best vacation ever and keep coming back just like I have!brEve H. Phoenix, AZ Sept. 2019 brbrThe perfect nesting place in paradise!brThe Nest villa is a very quiet, tropical nesting place that we have rented multiple times over the past 10 years. It is a 2nd floor condo that is very well equipped, comfortable and has most everything you need for a week’s stay. The inside is clean and modernized. The Bay, lagoon and sunset views from the main living area are truly amazing! It is located within walking distance of many local favorite eateries and yes, even a local brewery. The entire apartment complex consists of multiple small dwellings and is fashioned after an old keys style fish camp. The grounds are beautiful! The whole property is very tropical looking with several palm trees and flowering foliage. The villa also has a huge deck that overlooks the back yard, boat lagoon and Florida Bay. There are chairs there as well as a barbecue and table for dining outdoors. The lagoon is deep and wide enough for my 21 ft. boat and there are fish cleaning tables and fresh water hoses available. Don is a pleasure to do business with and makes the whole rental experience a breeze! Looking forward to returning again soon! We LOVE this place! brEd and Wendy Stuart, Florida June 2019 brbrGreat Place!brMy wife and I stayed in February 2017 and we are going back. Need I say more Great place, beautiful setting, excellent location, wonderful fishing, … the perfect vacation.brMike B. Washington DC Feb. 2017 brbrAwesome CondobrThis condo has such a great location and beautiful views. We walked to a few restaurants & drove short distances to others we love. It was also great being able to just cross the street to spend time at the Islamorada Beer Company! The condo itself has a great layout & is well stocked. The beds are so comfortable & the 2 baths are very nice. Everything was so wonderful that we've already booked for a week this December.brSusan W. Old Hickory, TN Dec. 2016 brbrBest weekly rental in Islamorada!brI've stayed at the Nest numerous times and will be there for my I believe my 5th time this summer 2018. The villa is located on a beautiful, tropical property and is meticulously maintained. My favorite feature of the lot itself is the protected basin to safely tie-up your boat, clean fish and mingle with the other are mostly repeat customers that you get to know over time. Inside the Nest you want for nothing, it has everything that you're used to at your own home, all of the electronics and appliances work as they should, linens are clean, bathrooms and the rest of the place are immaculate. The Nest has a private deck for laying out in the sun then grilling your fish for dinner, the sunset views are absolutely unforgettable. Stop clicking and book the Nest, you'll be glad that you did!brTony B. St. Petersburg, Florida August 2016

Villa

The Nest Villa & Marina with boat ramp, sun terrace, water views. Pet friendly!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$548.6

Little Bay Lower Level - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Lower Duplex is a 1,500 sq ft unit with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the Bay. Master bedroom: queen and twin murphy bed. Guest bedroom: two twins. Living room: sofa sleeper brbrThis unit comes equipped with central a/c and ceiling fans. The Lower Duplex shares with the other two units loads of outdoor furniture and BBQ, large private boat basin with 12' X 25' Chickee hut and 12' X 25' Pergola, bait prep station, freshwater shower and power on the dock. The spacious front yard is enhanced by Tropical Landscaping and offers a large circular driveway with plenty of parking for cars and trailers. brLocated in heart of Islamorada within walking distance to water & land activities, restaurants, shops, and more! The Lower Duplex can be rented individually or in combination with the entire Little Bay Compound. brbrIf 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.brVR-24-0335 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.

Charming 2-bedroom open water view home in Islamorada, perfect for 6 guests.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$456.64

VR License #24-4011br132 Anglers Way is an Adorable Key West style home in Anglers Reef. Small gated community located at MM 85 in Islamorada. Beautiful oceanfront pool, two beaches and a very convenient marina just stops from your front porch. brCall me for more information 305-240-0592.br Two bedrooms and two and a half baths with all the comforts of home. The master bedroom is a king size bed and the guest bedroom has two twin size beds with twin trundles underneath. brThere is a very nice living room with a sleeper sofa and dining room set up downstairs and all the things you would need to create a gourmet meal in the kitchen.brbrDock included in pricing. 31'max length and 9' bridge height.brbrPlease note, as of Aug 1, 2024. you will no longer be able to store a trailer outside the gate on the grass any longer. Trailers fitting under the carport are able to be stored there. Otherwise, we can recommend local storage lots you can contact.

132 Anglers Reef Islamorada- POOL, DOCK, BIKES INCL

Islamorada, Florida, United States

Bed

Bath

Sleeps

$675.0

This house is the perfect home base for your trip to Islamorada. With three cozy bedrooms, including a king bed and four twin beds, guests will find plenty of space to relax. Two bathrooms add convenience for everyone in your group. You can enjoy the amenities of a full kitchen. The house stays comfortable year-round thanks to air conditioning. We hope you enjoy what our place and Islamorada has to offer.

Ocean Front House: 3-bedroom house in fantastic Islamorada with cool AC

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1089.78

Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, including a fully equipped kitchen and an outdoor grilling area. Enjoy the privacy of your own pool and patio that extend from the living area. Located in the very heart of Islamorada, where you can explore its vibrant culinary scene with some of the best restaurants, breweries and live music in town. Choose from Square Grouper, Pierre's and Morada Bay to Green Turtle Inn, Florida Keys Brewery or Islamorada Beer Company. To experience more of what Islamorada has to offer, take part in various activities, such as visiting the Theater of the Sea or Founders Park, kayaking or paddle boarding, or even chartering a boat for deep sea fishing or diving at one of many marinas around town. brGolf cart rental available at daily or weekly rates.brbrPlease note, this property is located in a brand new development with ongoing construction on the houses closest to the water. Our house is situated in the center of the development, therefore, the construction should not interfere with the vacation experience.

Coastal Retreat ~ Brand New 4-Bedroom Home in the Heart of Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$868.58

Perfect vacation home for those who want to experience privacy and paradise in the Florida Keys! The house features plenty of parking space, both covered and uncovered, as well as a 75-foot dock, a dock-side chickee hut, and easy deep water access to the Bay and Ocean. Inside, the home has been updated with wood-look ceramic floors, a modern kitchen and bathrooms. The main-floor bedrooms are comfortable for guests and family, while the third-floor primary suite is a true oasis with a walk-in closet, a private deck overlooking the water and mangroves, and a luxurious bathroom. Port Antigua offers a private Homeowners' Beach with tiki huts and grill stations along a white sandy beach. Att: renting golf cars and boat lift separate. Contact host

15% to 20% OFF LUXURY HOUSE CLOSE TO THE OCEAN IN PORT ANTIGUA

Islamorada, Florida, United States

Bed

Bath

10

Sleeps

$517.01

125 Porto Vista Ct - No shoes, No shirt, No problem! In this Pt Antigua Pool Home, you will need to go nowhere to have an incredible Islamorada vacation! brStep inside this modern, updated, three-bedroom two bath and you'll never want to leave. The spacious open floor plan provides plenty of room for you and your guests to relax after a long day of fishing. Outside is where you'll really want to be hanging out making cocktails in your summer kitchen and splashing in the pool or fileting your daily bounty at the fish cleaning station. Best part, there's plenty of dockage for 2 boats in the deep-water canal! brPlease note, this house is only available from December to April on a monthly basis. 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 3-bedroom canal getaway in Islamorada, perfect for families!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$290.62

Enjoy camaraderie with family and friends in this well-appointed, three-bedroom, ranch-style house in a lovely, private, Atlantic oceanfront, small gated-community setting; complete with large heated community pool and protected cove, and deep-water boat slip. Fishing boats, captains and crew abound in Islamorada's fishing capital environment. Rest, relax, breath in the sea air, watch sunrise and sunset, explore the local shops and restaurants, read a book at the pool, snorkel, scuba, ride bikes, walk with leisure, take naps, grill your catch. Nestle in, be casual, and love all the Florida Keys have to offer!

Coral Cove Resort - ‘A Fisherman’s Dream’

Islamorada, Florida, United States

Bed

Bath

Sleeps

$771.01

Relax and enjoy the Florida Keys lifestyle and outdoor living with full wrap around terraces. PLEASE NOTE: 28 night minimum rental. Seasonal rates available.brbrThe SpacebrbrRecently renovated and beautifully furnished!brbrPool, tropical seas, fab fishing, boating, caribbean breezes, local restaurants and entertainment. Fun for the whole family.brbrNone. Local contact provided on reservation.brbrVenetian Shores is the premier deep water luxury private community in the Florida Keys with access to both the bay and ocean side of the keys from Snake Creek. Great restaurants and activities in the area for the whole family to enjoy.brbrBoat, Cars and Bikes (bring your own...;)!brbrPool, tropical seas, fab fishing, boating, caribbean breezes, local restaurants and entertainment. Fun for the whole family.brbrLocal contact provided on reservation.brbrVenetian Shores is the premier deep water luxury private community in the Florida Keys with access to both the bay and ocean side of the keys from Snake Creek. Great restaurants and activities in the area for the whole family to enjoy.brbrBoat, Cars and Bikes (bring your own...;)!brbrPool, tropical seas, fab fishing, boating, caribbean breezes, local restaurants and entertainment. Fun for the whole family.brbrLocal contact provided on reservation.brbrVenetian Shores is the premier deep water luxury private community in the Florida Keys with access to both the bay and ocean side of the keys from Snake Creek. Great restaurants and activities in the area for the whole family to enjoy.brbrBoat, Cars and Bikes (bring your own...;)!brbrPool, tropical seas, fab fishing, boating, caribbean breezes, local restaurants and entertainment. Fun for the whole family.brbrLocal contact provided on reservation.brbrVenetian Shores is the premier deep water luxury private community in the Florida Keys with access to both the bay and ocean side of the keys from Snake Creek. Great restaurants and activities in the area for the whole family to enjoy.brbrBoat, Cars and Bikes (bring your own...;)!brbrPool, tropical seas, fab fishing, boating, caribbean breezes, local restaurants and entertainment. Fun for the whole family.brbrLocal contact provided on reservation.brbrVenetian Shores is the premier deep water luxury private community in the Florida Keys with access to both the bay and ocean side of the keys from Snake Creek. Great restaurants and activities in the area for the whole family to enjoy.brbrBoat, Cars and Bikes (bring your own...;)!brbrGuest AccessbrbrPool, tropical seas, fab fishing, boating, caribbean breezes, local restaurants and entertainment. Fun for the whole family.brbrInteraction with GuestsbrbrLocal contact provided on reservation.brbrThe NeighborhoodbrbrVenetian Shores is the premier deep water luxury private community in the Florida Keys with access to both the bay and ocean side of the keys from Snake Creek. Great restaurants and activities in the area for the whole family to enjoy.brbrGetting AroundbrbrBoat, Cars and Bikes (bring your own...;)!

Islamorada Island Getaway

Islamorada, Florida, United States

Bed

5

Bath

8

Sleeps

$482.08

Welcome to 137 Ocean Lane in beautiful Islamorada—your private slice of paradise in the Florida Keys. This charming 3-bedroom, 3-bath home is designed for easy island living, with a spacious layout, coastal furnishings, and absolutely insane open ocean views from nearly every room in the house. The upstairs master suite features its own private balcony—perfect for sipping coffee at sunrise or unwinding under the stars. Downstairs, the main living area opens to a fully screened-in porch set up for dining, so you can enjoy meals with the ocean breeze and none of the bugs.brbrEach bedroom offers space and comfort, with bathrooms thoughtfully placed nearby to give everyone a little privacy. The kitchen is fully stocked and ready for everything from quick breakfasts to full seafood feasts. Whether you're here with family or friends, there's plenty of room to spread out and make yourself at home.brbrTucked away in a quiet neighborhood but just minutes from all that Islamorada has to offer—world-class fishing, local restaurants, and island adventures—you'll get the best of both worlds: peaceful mornings, salty air, and a front-row seat to some of the best water views in the Keys. Come settle in and experience laid-back living with an unbeatable view.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.

Relax in this spacious 3BR home in Islamorada with a private pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$348.87

Tucked away in the sought-after community of Venetian Shores, this 3-bedroom, 2-bath canal-front home is designed for easy Keys living. From the moment you arrive, you'll feel the relaxed island vibe with a private boat lift, shady tiki hut, and a bubbling hot tub waiting for you after a day on the water.brbrBring your boat and head out with ease—Venetian Shores offers some of the best access in Islamorada to both the Atlantic Ocean and Florida Bay. Back at home, the dockside tiki hut is the perfect spot to gather with family and friends, sip a cocktail, and watch the boats cruise by.brbrInside, the home is welcoming and comfortable with an open living space, well-equipped kitchen, and three cozy bedrooms for winding down after your adventures. The outdoor areas truly shine—whether it's morning coffee by the water, afternoons soaking in the hot tub, or grilling out under the palms.brbrThis home blends boating convenience with Keys charm, making it the ideal spot to enjoy everything Islamorada has to offer. 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.

Charming 3BR canal home in Plantation Key, perfect for family getaways.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$554.6

Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, water sport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Hotel Resort

Ocean view Studio w/kitchenette, Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

Sleeps

$685.14

Set along a private beach in Islamorada, La Siesta Resort & Villas features colorful cottages with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, watersport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbr✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Cottage

Oceanfront Cottage in Islamorada! Swimming Pool, Pets Allowed, Free Parking!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$606.34

Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, waters port rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Hotel Resort

Ocean Front Studio w/Kitchenette, Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

Sleeps

$603.0

Set along a private beach in Islamorada, La Siesta Resort & Villas features oceanfront studios with premium amenities. Guests enjoy heated pools, Sidecar poolside bar, watersport rentals, marina access, and shared benefits across three resort properties—including shuttles, dining, and leisure facilities.brbrThis listing is for a room within a hotel.brbr✦ Your room is 450 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Pool available all year.brAdditional features:br • Heated poolbrbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $55.13 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 per pet per day, with a max of 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ The front desk is open daily from 7 AM to 11 PM with your information and keys ready. After hours, you’ll be directed to a nearby sister resort for check-in.brbr✦ The required refundable security deposit is charged per night on a valid credit card.

Hotel Resort

Oceanfront Studio Queen w/Kitchenette, Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath