Vacation Home Rentals By Owner In Islamorada, FL

Welcome to Oasis4rent!brbrEscape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully appointed homes sit directly on the Atlantic with 200 feet of sandy beachfront, a heated saltwater infinity pool, and views of Alligator Reef Light on the horizon.brbrThe PropertybrbrMain House: 1 king bedroom (Tempurpedic adjustable), 1.5 baths, full kitchen, wrap-around porchbrbrGuest House: 2 bedrooms (queen + queen/full), 1 bath, full kitchen, ocean-view living roombrbrSleeps up to 8 guests across 3 bedrooms and 4 bedsbrbrWhat Makes This SpecialbrbrPrivate sandy beach — swim, kayak, or paddleboard from your backyardbrbrHeated saltwater infinity pool with unobstructed Atlantic viewsbrbr100+ palm trees, 60+ lit at night — the Keys' most stunning evening ambiancebrbr6 high-end bikes for exploring Upper Matecumbebrbr4 kayaks, 2 paddleboards, bocce ball, and cornholebrbrTesla and NEMA 14-50 EV chargerbrbrEnterprise-grade Wi-Fi covering the entire estatebrbrGated entrance for complete privacybrbrThe LocationbrWalk or bike to Italian Food Company, Bayside Gourmet, local breweries, and art galleries. Less than a mile from Publix. World-class fishing, snorkeling, and diving charters depart from nearby marinas.brPet-Friendly — Dogs welcome ($350 fee). They will love the fenced, grassy yard.brCoffee on the porch at sunrise. Dolphins passing just offshore. Margaritas by the pool at sunset. This is why it is called The Oasis.

Oceanfront Keys Escape | Private Beach & Pool | 3 Acres

Islamorada, Florida, United States

Bed

1

Bath

Sleeps

$770.63

ONE-OF-A-KIND VACATION HOME. Elegant living at its finest. You will never want to visit any other place. Large open space throughout the entire house. Beautiful dining area, open kitchen and spacious living room. Private pool. Porch with water view. Complimentary private beach for White Marlin Beach residents and guests.

ISLAMORADA DREAM

Islamorada, Florida, United States

Bed

Bath

Sleeps

$460.14

INTERIOR LOT—-NO ROAD NOISE—-BOAT SLIP AVAILABLE———Interior Painted Jan 2024---New Furniture in Family Room---Beautifully Decorated and So Comfortable!brbr*** This is a great house---beautifully furnished/well kept. Oceanview with two porches!***brbr*** NO ROAD NOISE. This house does not back up to the Overseas Hwy and is very quiet and secluded within Anglers Reef! ***brbr*** Please email and I'll answer any questions you have! ***brbr***** PLS BOOK YOUR WEEK(S) EARLY AS MANY WEEKS FILL UP 6-12 MONTHS AHEADbrbrWe are one of Islamorada's limited number of licensed weekly vacation homes, VR #25-0258 (State License #DWE5404378).brbrAngler's Reef is Islamorada's premier resort community located at MM85 (on the Ocean side) in the heart of the Florida Keys. Islamorada is known as the SportFishing Capital of the World. Our boutique gated community is made up of 52 luxury waterfront villas, inspired by Native Conch and British West Indies architecture, accompanied by a boat basin with 36 slips, a large heated pool, two sandy beaches, and quiet palm tree-lined streets. Quick boat ride or short kayak ride over to the world famous Islamorada Sandbar for fun in the sun or the Alligator Reef Lighthouse for snorkeling!brbrIslamorada is known as the Sport Fishing Capital of the World. The Gulfstream flows past the Florida Keys from 10-20 miles offshore and brings seasonal visitors like mahi, tuna, wahoo, dolphin, sailfish and marlin close enough to shore for small-boat fishermen. Tarpon and bonefish are also plentiful in the backcountry. There are plenty of captains that will provide day-trips for you if you are not bringing a boat along on vacation. Also, boat rentals are definitely available, if you'd rather be your own captain for the week (or two). brbrThe home's boat slip (with electric and water) fits a vessel up to 31 ft. (max ht of 9 ft) and is available for an additional cost of $500+/week. Deep channel out to the Atlantic. The neighborhood of Anglers Reef has stand-up-paddle boards and kayaks for use by renters. A Kayak waiver will be required in order to take advantage of these during your stay. brbrWater sports include diving, snorkeling, parasailing, windsurfing, kayaking, paddle boarding and more. Fine dining close by includes Ziggie & Mad Dogs, Chef Michael's, Morada Bay, Cheeca Lodge along with fun spots like Hog Heaven and Robbie's (to feed the tarpon). Bayside Gourmet is just down the road. It is #1 on Trip Advisor and a must-do for a wonderful meal! There is a Publix grocery just 1 mile south of Anglers Reef. brbrTheatre of The Sea (for dolphin and sea lion shows and interactive exhibits) is located nearby. Marathon is just a short ride down the Overseas Highway where you can visit the Dolphin Research Center and The Turtle Hospital for fun activities for adults and kids alike. brbrThree state parks that are worth a visit are close-by as well: brJohn Pennekamp Coral Reef State ParkbrBahia Honda State ParkbrLong Key State ParkbrbrKey West is less than two hours away. Definitely worth the drive!brbrEnjoy the expansive views and ocean breezes from the porches/balconies on the first and second stories. Upgraded Chef's kitchen with top of the line appliances, granite counters, and eat at bar. Kitchen is fully stocked with cookware, dishes and appliances. Weber gas grill outside. brbrOn the second floor, there are two suites which will sleep 6 comfortably. brThe Master Suite has a king bed, private bath and amazing porch with ocean views.brThe Guest Suite has 2 queen beds with private bath.brWasher/Dryer upstairs. brbrLinens, bath towels and beach towels are all provided and replaced often. We have lots of puzzles and games available. brbrBoat Trailer Storage is available close by. Ask owner for details. brbrCable and WIFI included.brbrTwo available covered parking spaces. brbrRentals are Saturday-Saturday. Exceptions please inquire with owner. brbrPictures and description are representative of accommodations provided but are subject to change.brbr***no trailer parking in carports***brbrNO PETS ALLOWED BY COMMUNITY LAWS

Anglers Reef Islamorada Ocean Views DOCK Beach Pool Boat Slip NO ROAD NOISE!

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$1182.86

Welcome to Islamorada- the Fishing Capital of the World.brbrOceanfront living doesn't get better than this. In the heart of Islamorada, this vacation home is located on the exclusive Millionaire's Row street. Once you enter into the private oceanfront estate, you have arrived in paradise!brbrThe house has two levels which are accessed via the outside staircase.brbrThe main floor is upstairs where you will find the living room, dining room, kitchen, laundry room and sun room with spectacular ocean views. There is also a reading nook in the sunroom with a small book library. Also upstairs is a master bedroom with a king bed, TV, and en suite bathroom. The second bedroom has two full size beds and a TV. There is a hall bathroom with a bathtub and separate shower. For the coffee lovers, we have provided a coffee bar. You can choose to make your coffee with a standard coffee pot, a Keurig, or a Nespresso machine. Enjoy!brbrThe first floor, patio level, boasts two bedrooms. The first spacious bedroom which is steps away from the pool and has an ocean view, features a king bed, a twin bed, TV, and a small refrigerator. The second bedroom has two full size beds and a TV. Both bedrooms share a large bathroom with a shared closet.brbrOn a hot day in the Florida Keys, it is nice to take a swim in the pool overlooking the Atlantic Ocean. The pool can be heated in the winter months at no additional charge. There are plenty of chaise loungers if you'd prefer to relax and catch some rays.brThe kids will have a great time playing in the sand and building sand castles with the sand toys provided. You can always take up a game of ping pong under the covered patio. brAnd of course, you'll probably want to take a dip in the ocean. The water is shallow so you can walk right in over the seawall and go for a swim. Depending on the tide, there could be some seaweed.brbrNamed for its stunning 350 foot pier, be sure to be on the lookout for the many fish and sea creatures in the ocean as you walk to the end.brbrFor your convenience, we provide:brbrInside the house:br- Ceiling fan in each bedroom, living room, and sun roombr- Smart TVs with 300+ channelsbr- Hair dryer in each bathroombr- High speed Internet with WIFIbr- Each bathroom has a pump bottle of shampoo, conditioner, and body wash.br- Welcome supplies pack of paper towels, toilet paper, small dish soap, and kitchen sponge.brbrOutdoors:br- 2 kayaks with life jacketsbr- Outdoor gas bbq and charcoal bbqbr- Outdoor bait freezerbr- Ping-pong tablebr- Sand toys for the childrenbrbr** Sleeps 10br** 7 Night Minimum / Saturday to Saturday Only**br** Pets permitted with prior approval**

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Islamorada, Florida, United States

Bed

Bath

10

Sleeps

$581.9

Your cozy getaway awaits in Islamorada at this superb house. With 4 bedrooms including a king, queen, bunk, and twin bed, this excellent property is perfect for families or groups of friends. Three bathrooms ensure everyone has space to freshen up after a day of exploring. Enjoy all that Islamorada has to offer when you stay at our place.

Beautiful two- story beach house

Islamorada, Florida, United States

Bed

Bath

Sleeps

$633.38

Come stay at the Salty Pelican in Angler's Reef! Recently updated 2 bedroom 2 bath plus a den downstairs with a pull out queen sofa. This magnificent home with amazing direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Home also overlooks the community pool. Anglers Reef is a quiet oceanfront community in the Florida Keys. Angler's Reef is a boutique complex of 52 homes inspired by Native Conch & British West Indies architecture. Quaint streets & walking paths wind through this village-styled retreat. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home's boat slip is available for rent with a deep channel out to the Atlantic ($500 per week. Let owner know after booking to add dock). Or launch your kayak from the private beach (kayak rentals available for drop-off). Built in 2007, this home has 2 bedrooms located on the 2nd floor, the master bedroom has a private porch with ocean views or lie in your king bed and enjoy the same view. Downstairs porch also has ocean views for morning coffee or cocktails. Second upstairs bedroom has 2 queen beds in it. Downstairs den has a double doors and a pull out queen sofa bed. Homes decor includes stainless appliances, granite counters, Brazilian wood floors upstairs and downstairs, 3 flat screen TVs with cable and TV APPs to watch your favorite shows. Home also has very fast WiFi.brbrIslamorada is synonymous with the best fishing - gulf, backcountry or ocean. There are plenty of guides, charters or boat rentals. You can also try for hogfish, snapper, mahi, tuna, bonefish, tarpon, snook, & more. Right at the Anglers Reef docks you can catch mangrove snapper, ladyfish, jack crevalle, moonfish, grunts, mullet & barracuda depending on season. We had one lucky vacationer catch a 70 pound Tuna right off the docks.brbrFor those who don't like fishing there is still a ton to do which is one of the reasons we chose Anglers Reef. The development and the Islamorada area have a lot to do for people who are not into fishing. Just hanging at our home and looking at the gorgeous pool area in the back of the home and the great views of the ocean from our home is enough of a full day for some. brbrEnjoy our spacious deck with a book or cocktail and the views of the turquoise waters and ocean breeze. Or just walk off the porch and swim in the large community pool (heated in winter and cooled in summer!). And if that's not enough you can take a stroll thru the community or relax on the private beaches or you can launch Kayaks and Paddle boards right off our beaches.brbrRestaurants: a short 5 minute walk are Hog Heaven, Smugglers Grill and the Island Grill. By car a few miles away are lots of oceanfront or bay front restaurants to eat at. All are amazing. See our recommendation book in the home.brbrAttractions: Swim with dolphins at Theater of the Sea 1/2 mile south. Founders Park is just a mile north with concerts and lots to do. The Islamorada Chamber of Commerce visitors center is also near the entrance to Founders Park for local info as well as affordable postcards, posters, T-shirts and books.brbrGrocery & Other Shopping: Publix just opened at MM83 on the Island and is just 2 miles south of the home. For quick items Trading Post is a little further south. There is also a Winn Dixie a few minutes north (around Mile Marker 91 in Tavernier. There is also a West Marine, Bass Pro Shop and other cool little stores around the town.brbrParks in Islamorada, Village of Islands: Just 2 miles north is Islamorada Founders Park at MM 87 Bayside, which offers activity or relaxation for the whole family. An Olympic-sized pool with diving area, a shallow water beach, water sports rentals, ball fields, fishing jetty, bocce, tennis and basketball courts, vita course with 18 exercise stations, multi-purpose path, skate park and dog park all are within the 40-acre park. Fees may apply. Village municipal parks also include the Islamorada Library Beach and Anne’s Beach. There is the Windley Key State Geological Site, a state park, at the site of a former coral rock quarry. In addition to shady walks through unique foliage, fossils of sea creatures can be seen throughout the park. A free guidebook is available at the visitors center for use during your stay in the park. Islamorada also offers an 18-mile bicycle path that extends the length of the Village.brbrScuba/Snorkel! : Islamorada, long recognized as the 'Sport Fishing Capital of the World,' is now an icon among sport divers for a similar reason: a massive population of tropical marine life. High profile coral heads and broad ledges shelter huge congregates of French grunt and goat fish, while regal queen angelfish casually graze amid the reef recesses. Friendly green moray eels swim freely along the spur-and-groove channels, and reclusive nurse sharks lurk beneath the overhangs. Islamorada offers a wide variety of shallow coral reefs, mini walls, shipwrecks, and even an underwater habitat for scientific research, the Aquarius. To learn more about Islamorada or any other manner of local lore, stop by the Chamber of Commerce at MM 82.5.brbr*The Eagle - This 287 ft ship was intentionally sunk in 110 ft of water as a dive attraction, cloaked in sponge & coral, populated by grunt, harpoon & jack. *Davis Reef - Reef revered for its incredible concentration of grunts & schoolmaster snapper, as well as several amiable resident green morays, long accustomed to benign interaction with the dive masters. *Alligator Reef - Now marked by a 136-ft-tall lighthouse, on this spot in 1822 the USS Alligator grounded & sank while protecting a convoy from pirates; remains of the wreck are the twin piles of ballast stones, but the coral reef - in just 25 ft of water - is vibrant and alive. *Conch Wall - Offering a precipitous sloping wall & captivating concentrations of barrel sponge & gorgonia punctuating seafloor. *Crocker Wall - A 450+-foot-long wall in 50 ft of water. The wall has a 30 ft decline and features grunts, yellow tail & grouper with spur-and-groove coral & block coral.brbr*Pickles Reef - Reef's minutia in 15-25 ft of water.

Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach, plus Den

Islamorada, Florida, United States

Bed

Bath

Sleeps

$461.91

Discover the serene escape of Windy Cove 1, nestled in the enchanting heart of Islamorada. This stunning three-bedroom condo boasts a mesmerizing view of Windley Key, making it the perfect backdrop for your next getaway.brbrThe bright and airy ambiance welcomes you as you enter. With a spacious layout, Windy Cove 1 features one King bedroom, one Queen bedroom, and a light-filled room with two Twin beds, comfortably accommodating up to six guests. The two well-appointed bathrooms ensure convenience during your stay.brbrEnjoy quality time with family or friends in the cozy living area, equipped with a Smart TV and comfortable seating. The modern kitchen invites culinary creativity, featuring a stove, refrigerator, microwave, dishwasher, coffee maker, and ample dishware – everything you need to prepare and savor delicious meals together.brbrStep outside to find your personal oasis! The property includes a heated, fenced pool perfect for relaxation, complemented by a spacious deck with sun loungers and a grill for outdoor barbecues. Whether you want to sip your morning coffee on the balcony or unwind under the stars, Windy Cove 1 offers the ideal outdoor living space.brbrLocated just minutes from local attractions, you'll have the chance to explore stunning beaches, renowned dining, and exciting water activities that Islamorada is famous for. This property offers not just a home, but a true vacation experience.brbrDon't miss the chance to create unforgettable memories at Windy Cove 1. Book your stay today!brbrVacation Rental License# 24-0384 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.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.

Windy Cove 1: 3-bedroom condo in Islamorada with pool access and stunning views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$521.08

***POOL Built in July 2019; Tropical landscaping installed 2020/2021 with great privacy***brbrLocated in Islamorada the premier Key of the Florida Keys, which is known as the Sports Fishing Capital of the world. Islamorada is actually made up of five Keys and this beautiful 3-story home is located in Lower Matecumbe Key, which in my opinion is the best of all. On visiting the property, you'll first notice that it's located on a quiet road at mile marker 76.5 located just 5 houses down the canal from the beautiful turquoise waters of the Atlantic Ocean, and a straight shot to Alligator Reef Lighthouse. This is the perfect place to spend your next vacation with family and friends. This home was completely gutted and remodeled in June 2015 and everything is brand new. This is a non-smoking home. The remodeling and décor are very high-end and everything is tasteful, high quality, spotless, and again NEW! The furnishings, appliances, electronics and fine art were done with my family in mind as a true second home for us and not from a rental property perspective. This home includes many great pieces of art from world-famous Barry Barnett and world-renowned fine art photographer Alan S. Maltz who is known for his work in the Florida Keys and throughout the State. We appreciate the added touch and conveniences, which includes hi-speed WiFi (100+ Mbps download speed), updated Kitchen which includes all high-end (LG) stainless steel appliances, an abundance of kitchen gadgets and appliances from blenders to griddles to Riedel wine glasses, 2015 Samsung 55” LED Smart TV, Apple TV, NetFlix and many other niceties.brbrThis home is only five houses away from the ocean, so you are literally ONE MINUTE away from the crystal clear waters of the Atlantic Ocean. The house also includes unlimited use of two Scupper Pro Ocean Kayaks to keep you active. We are walking distance (~ 1 mile) to Robbie's Marina, home to a large resident population of tarpon that you can watch and feed. brbrThe home is truly the ultimate in tropical living. You will find the kitchen is fully equipped with all you need. Wood cabinetry, granite/marble countertops, LG stainless steel appliances with all the accessories including a Keurig coffee maker and a regular coffee maker and all the kitchen utensils and accessories that you need to provide gourmet meals, including a great selection of quality spices. A Smart Samsung TV, with Xfinity cable that includes over 140 channels, and if that is not enough the home also is equipped with an Apple TV and Netflix if you want to connect to your own account and download the movies and shows that you have been meaning to get to. I can assure you, that if TV and digital entertaining is what excites you, our hi-speed wi-fi and technology will suit even the most discriminating guest. brbrVacationing over the years with another family, it always came down to “who gets the Master bedroom” (we switched off every other year), so one of the great things about this home is that it comes with TWO spacious master bedrooms and these are very large bedrooms.brbrThe Master bedroom on the 3rd floor is furnished with a King size bed. It also has a dedicated working area for those individuals that need to mix a little work with play. This bedroom has its own dedicated A/C unit, so you don’ t have to worry about compromising the temperature in the rest of the house. The sliding doors in this bedroom open to the third-floor balcony/terrace, which will provide you with a glimpse of the ocean, a nice ocean breeze and some peace and quiet if you want to get away from others in your group. It’s a great location for that morning coffee and watching the beautiful sunrise every morning or my personal favorite laying on the lounge chair late at night and gazing at the stars. This bedroom also features a magnificent master bathroom with an extra-large shower which features a rain-drop showerhead as well as a hand-held shower. brbrThe Master bedroom on the 2nd floor is also furnished with a King size bed This room is even larger than the MBR on the 3rd floor. It has direct access to a bathroom and the laundry room. brbrBoth master bedrooms include ample drawer space for all of your clothes and it is of the same quality of what you will find at a Ritz-Carlton, including the mattresses. brbrThe 3rd bedroom has three twin beds. Plus we have a sleeper sofa (queen-sized). brbrThe family room, dining room, and kitchen open up to the tropical outdoors environment through 3 sets of sliding glass doors. This set of expansive sliding glass doors opens up to the veranda where you can sit and soak in what is going on downstairs or wave at the boats going by. Throughout the entire 2nd floor and 3rd floor is hardwood floors. The 1st floor is marble throughout. Every window, door, and sliding glass door in this house is hurricane impact, which is great for protecting the home from a storm but does a superb job in making this home super quiet. Also, every window on the 2nd and 3rd floor, have custom-made plantation shutters that do an amazing job in setting that island feel and keeping the temperature in the home cool. brbrFor the Fisherman, a stay at our location puts you four houses from the Atlantic Ocean, but backwater access is just minutes via Indian Key Channel or world famous fishing channels number #2 or #5. This home includes 90 feet of dockage on the canal coming straight from the ocean which includes an additional 30-foot cut-in slip, making it a great place for any boat. This private dock provides running water and a large (6-foot) custom-made fish-cleaning station. You will also find in the garage a deep freezer for storing an ample supply of your bait, so you don’t have to make those daily trips to the local bait store or marina. Located nearby (very close) is a local public boat ramp that is free to use as well. With this effortless access to the open ocean, and an abundance of fishing and tackle shops, such as Bud and Mary’s Marina, World Wide Sportsman (aka BassPro), Sandy Cove, Calusa Cover Marina, and more, this location will satisfy fishers of all skill levels. brbrFor rest and relaxation, the outside patio on the 1st and 2nd floor offers a comforting open space complete with many resort-like lounge chairs, tables and chairs, and a stainless steel Weber grill with side burner. The home also comes with two beach cruiser (bikes) for those that enjoy a little sightseeing on two wheels. There are many restaurants within three miles to visit by boat, car, or bike. brbrWe know that you will truly enjoy our home and all the extra features that it provides. We include paper towels, soap, shampoo, dish-washing liquid, laundry detergent, sugar, spices, and much more. We look forward to sharing our home with you very soon. I will be waiting for your call/email to tell you even more about the house and the area. Also, if you are looking for recommendations on things to do or places to eat, I will email you my personal guide to the Keys. I will share this guide with you regardless of whether you stay at our home or not.

Luxurious Home with POOL

Islamorada, Florida, United States

Bed

Bath

Sleeps

$346.07

Stay comfortably in Islamorada at this 3-bedroom house. This phenomenal property offers a tranquil escape for guests seeking a cool and relaxing vacation. With 2 king beds, 1 twin bed, and 1 queen bed, you'll have plenty of space to unwind and recharge. Enjoy the convenience of amenities like a washing machine, AC, WiFi, a hair dryer, and an iron. Immerse yourself in the serene surroundings and create lasting memories. Whether you're lounging in the cozy living area or exploring the beautiful city, this is the perfect home away from home. My grandchildren, who manage the property, will be available to answer any questions while you stay at our little OASIS.

Tranquil 3-bedroom house in enchanting Islamorada with WiFi, AC, 70 foot dock.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$909.37

Rare Summer Openings! Your Private Resort Awaits in Islamorada brbrIf you’ve been dreaming of an island escape with all the luxury of a high-end resort but none of the crowds, this is your chance.brbrEscape to the islands in your own private resort. This Florida Keys home feels like your own private tropical oasis located in the heart of Islamorada. This five bedroom, 7 1/2 bathroom home features a spacious covered downstairs living area poolside, decorated in tropical themes of bamboo and coral. This area encompasses two living areas, a large spacious bar and grill, a large screen flat TV, outdoor pool table and dining area, all poolside along the oversized pool and spa. brbrInside, you’ll find five bedrooms, each with en suite bathrooms. The large open great room has a gourmet kitchen, spacious living room and dining room, and opens to a large, screened patio with a second bar overlooking the canal and Snake Creek.brbrThe master suite encompasses the entire third floor and features large bathroom with dual vanities and walk-in shower, a private sitting room with wet bar, a private screened patio, and an open sundeck. brbrFor convenience, and elevator connects all three levels.brbrI am the former rental manager for Century 21 Circle based out of Key Largo and Islamorada Florida i

Venetian Shores 5BR/7BA Home with Pool, Spa & Boat Lifts

Islamorada, Florida, United States

5

Bed

6

Bath

10

Sleeps

$775.77

Casa De Bliss - Canal front Venetian Shores...Unwind on your trip to the Keys at Casa De Bliss. This four bedrooms, four-and-a-half-bathroom house is located on a deep-water canal in one of Islamorada's most sought-after neighborhoods, Venetian Shores. The spacious main living area and open kitchen are perfect for preparing meals together while enjoying the company of family and friends. Sneak away to your private master suite on the third floor and continue up to the crow's nest to enjoy a private view of the sunrise or sunset. The main level has two guest ensuites. The ground level includes an additional guest bedroom and bathroom as well as an entertainment area. Enjoy your private pool and hot tub! Entertain with your outdoor kitchen featuring a propane grill, Blackstone flat top grill and smoker. Never miss your favorite sports on the 85 outdoor TV. Fishing enthusiasts will appreciate the thought put into the outdoor area from the custom stainless steel fish cleaning station to the onshore bait pen and much more. Direct access to both the ocean and bayside via Snake Creek for easy access to fishing, diving and local waterfront restaurants.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.

Experience luxury at Casa De Bliss, a spacious 4-bedroom canalfront retreat in Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$205.72

Get ready to relax in this 3-bedroom townhome in Islamorada. The space features one queen bed and two king beds, perfect for a group or family. With two bathrooms, each equipped with a shower and hair dryer, getting ready is a breeze. Guests enjoy a nice balance of comfort with heating and AC to keep the temperature just right. This awesome townhome offers a cozy, welcoming vibe that makes it easy to unwind after a day of adventure. We think our place will help you experience everything Islamorada has to offer.brbrAdditional rulesbr- No Pets are allowed in the entire complexbr- No Partiesbr- Be courteous to neighbors

Islamorada Getaway Townhouse

Islamorada, Florida, United States

Bed

Bath

Sleeps

$855.91

Vacation Rental License No VR-001 brWEEKLY RENTALbrLocated on the peaceful upper Keys, in Islamorada, this home is situated in the quiet residential neighborhood of Venetian Shores MM 86. Immediate access to ocean and Bay side off of Snake Creek. Islamorada is is just 75 miles from Miami and 86 miles from Key West. The average temperature is 80 degrees and 78 degrees for the water. Islamorada sits between the clear waters of the Florida Bay and the Gulf of Mexico, it is bestowed with a Coral Reef three to five miles offshore that is filled with spectacular life. brTwo story homebrThis 3 bedroom, 3 bath, private home is equipped with many extras including this heated (at 80-82 degrees) swimming pool that is partially shaded so you can enjoy floating with a cool drink leisurely. WIFI ready. This vacation gem boasts large rooms furnished in rattan and decorated with a tropical flair. You can see this view from the living room, dining room, and kitchen as it has four large sliding glass doors opening upon our large deck. brbrFirst bedroom has a queen-size bed with a private full bathroom and plenty of natural sunlight. TV in the room .New tiles, this room has been totally renovated with it great poster bed. The second newly tiled bedroom has king bed, with TVbrFully renovated kitchen with stainless steel appliances, granite counters, Flat screen computer with high speed internet. Also WIFI ready. brOur master suite, all tiled. It is at the pool level. You can just walk-out in the morning and enjoy the refreshing view and sit on the deck, this view is of the large sitting room with the king-size bed in the background. It opens totally up on the pool deck with sliding glass doors. Heated kidney shape pool at 82 degrees , dogs permitted upon request $300 deposit per pet

Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$503.34

Spacious, open layout designed for ultimate comfort and convenience. The fully equipped kitchen flows seamlessly into the cozy living and dining areas, all boasting breathtaking canal views. Enjoy your morning coffee on the terrace as you watch the sunrise over the pool and waterway—this is truly island living at its best.brbrThe home offers three bedrooms upstairs, including a spacious primary suite with a bath and a luxurious closet. The two guest bedrooms share a full bath with dual vanities. Downstairs, the additional family room and fourth bedroom offer even more space to spread out. A wet bar off the pool area makes entertaining a breeze, and the private, fenced backyard provides a true tropical escape with lush turf, a Tiki hut, and a stunning pool area.brbrThis property is ideally located for boating enthusiasts, with a boat ramp at the local Founder’s Park. Direct access to Snake Creek, the Bay, and the Ocean makes this the perfect base for water lovers.brbrConveniently located near shopping, dining, schools, art galleries, and local breweries, this home offers the ultimate combination of tranquility and proximity to all the best of Islamorada. brbrBedroom 1 - King BedbrBedroom 2 - Queen BedbrBedroom 3 - Queen BedbrBedroom 4 - Bunk Bed - 2 Queen Mattresses

Pool Home in Venetian Shores

Islamorada, Florida, United States

Bed

Bath

16

Sleeps

$1516.9

82754 Overseas Highway - OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering five bedrooms and three full baths on two living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully equipped kitchen with the dining room overlooking a lush private garden. The spacious living room features a natural keystone wall-framed fireplace with cypress mantle, a full wet bar, and separate bath, which also opens to the pool area. brThe private, downstairs south wing offers three bedrooms and one full bath with a 5th bedroom off the kitchen. The 2nd level master bedroom suite with private vanity & master bath has its own fireplace & bayside veranda. brThe downstairs sliding glass doors open to the bayfront pool & elevated deck with hot tub. There are multiple decks for sunbathing and spectacular sunset-viewing. The expansive dock with its own fish cleaning table wraps around the basin for boats, water toys, and great fishing fun! The beach offers a wade-in area for snorkeling in the bay or an easy launch for kayaks. brThis vacation home is secluded yet situated in a perfect location for walking to restaurants & local shops! Sorry, no pets allowed. brVACATION RENTAL LICENSE: 24-0308 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.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. 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.

Stunning 5-bedroom home on Upper Matecumbe, Islamorada, perfect for 10 guests.

Islamorada, Florida, United States

5

Bed

Bath

10

Sleeps

$656.66

This beautiful home is nestled in the quiet neighborhood of Venetian Shores. It sits right on a deep water canal minutes to the Ocean or Bay. The house has heated and chilled pool along with a jacuzzi that sits next to the water. It has 4 bedrooms (all bedrooms are on second floor) and 4.5 bathrooms (3 upstairs) with a half bath on the ground floor & a FULL bathroom right off the pool area. This home also features a game room with arcade games and full billiards pool table. 28 day rental only.brbr4 Bedrooms with 1 king bed and 3 queens in the addition rooms. This home has a chilled and heated pool with a stand alone Jacuzzi. This home is also equipped with billiard pool and arcade games for those not so often raining days.brbrMaster bedroom has ensuite bathroom with walk in shower and private attached office space overlooking the water. brSecond bedroom has queen bed with ensuite bathroom. brThe two additional bedrooms feature queen beds as well with a shared unattached bathroom. brbrAnother full bathroom with shower as available next to the pool deck.brbrGuests will gain access to this property through the front door with a keyless entry lock. Guest will be given code 1 day before arrival with check in-instructions.brbrWe are available 24/7 for all your questions and needs. Don’t hesitate to contact us through text or phone.brbrVery quiet neighborhood of Venetian Shores. Great neighbor hood to walk or get some exercise on the two bikes provided. We are pet friendly so please be respectful and pick up after your pet and keep our neighborhood clean. No traffic besides those of the neighborhood.brbrWe also recommend bringing your own vehicle or renting one for the duration of your stay as its the best way to explore the long and vast Florida Keys. There is also free taxing service (Freebee) and Uber and Lift is available upon request.brbrDue to our regulations in the Village of Islamorada, it is only available for 28 days or more. Certain months will be blocked off as we love to use our own home certain times of the year. Please don`t hesitate to reach out directly if you have any question about this listing.brWe do not have dock space at this time as we keep our personal boat on the lift, however we are in the process of getting a new dock built to accommodate a 28ft to 30ft boat by the end of this year ready for the next season. We apologize for the inconvenience and hope you will keep us in mind for your future adventures if you need dockage for your personal boat. Do not hesitate to reach out if you have any questions regarding marine resources as there is a marine within 1 mile that can hold your boat for a fee.

Turtles Nest Islamorada Getaway 28 day rental

Islamorada, Florida, United States

6

Bath

Sleeps

$250.11

Welcome to Executive Bay Club U2!brbrLocated in the heart of Islamorada, this fully upgraded townhouse offers everything you need for the ultimate Florida Keys getaway. One of the few units featuring 3 bedrooms, 3 full bathrooms, and a loft with additional sleeping space, this home is designed with both comfort and convenience in mind. The modern kitchen is fully stocked for preparing your favorite meals, while the tastefully decorated living room and back patio provide the perfect spaces to relax after a day in the sun.brbrAt Executive Bay Club, the activities are endless. The pool and clubhouse were fully remodeled in summer 2025, offering fresh, modern accommodations for guests to enjoy. Spend the day lounging at the private beach, cool off in the sparkling pool, play a round of tennis, or take a sunset stroll to the end of the dock. brbrDirectly adjacent to Executive Bay Club is Founder’s Park which provides even more ways to enjoy island life, including an Olympic-sized swimming pool, kids splash pad, beach, playgrounds, fitness and walking trails, basketball and pickleball courts, sports fields, picnic areas, and even a golf driving cage (park entry fee applies). For boating needs, please note that Executive Bay Club does not provide dockage for guests. However, Plantation Yacht Harbor Marina, located within the same facility as Founder’s Park, offers secure dockage with 80 slips available by the day, week, month, or year. Each slip includes electric, water, sewage pump-out, and fuel sales, along with access to a boat ramp and dedicated trailer parking.brbrDon’t miss the chance to make this exquisite townhouse your home base in the Keys. brbrFor more information or to book your stay, contact Coastal Vacation Rentals of the Florida Keys at (305) 664-0077. Instant quote prices and calendar availability are subject to change without notice and are not guaranteed. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one of our associates to confirm pricing and availability.brbrHave any questions Feel free to ask away! Coastal Vacation Rentals of the Florida Keys is located in the heart of Islamorada and has a full office staff to ensure you have the best vacation possible.brbrReservation Deposit & Cancellations: A reservation deposit equal to one-half (50%) of the total reservation amount is due at the time of booking. TENANT shall be entitled to a refund of the one-half (50%) reservation deposit, less any non-refundable fees, if the reservation is cancelled at least 60 days prior to the occupancy date. The remaining balance, including any required security deposit, is due no later than 60 days prior to the occupancy date. If the cancellation occurs within 60 days of the occupancy date, the full reservation amount shall be non-refundable. If the booking is made less than 60 days prior to the occupancy date, the full reservation amount shall be due at the time of booking, and TENANT shall not be entitled to a refund of any amounts paid in the event of cancellation. As an exception to the foregoing, TENANT shall be entitled to a refund of all amounts paid if COASTAL re-rents the property for the same amount and for the full rental period. If the property is re-rented for fewer days or at a lower rate, COASTAL may deduct from the refund the difference between the total amount due under TENANT’s original reservation (including all taxes and fees) and the amount received from the subsequent rental.

Executive Bay Club U2 ~ 3 bed / 3 bath + Loft Townhouse in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$240.79

Clean & updated oceanside canalfront home. Located at desirable brLower Matecumbe in the Village of Islamorada, brM.M.74.Boat ramp on property,just pull up with your boat, launch, and bryour off to fish or dive. Excellent deepwater dockage for up to a 29' boat,brfish cleaning station. Direct ocean & bay access. All the brcomforts of home. Two bedroom home-First bedroom -1 king Second bedroom-2 Twin & in the living room is a full size futon. Plenty of room to park brboat trailer and your vehicles in the front yard.

Deep Water Canalfront Home W / Boat Ramp

Islamorada, Florida, United States

Bed

Bath

Sleeps

$662.92

Islamorada Oceanfront home located directly on a private beach; enjoy swimming snorkeling, and ideal for kitesurfing! Perfect for taking a stroll on the beach and/or just enjoying the view of the Ocean. Enjoy the Tiki Hut & Hammock, BBQ Grill and more. And if you are bringing a boat, the Caloosa Cove Marina is just 2 minutes away! (The is no dockage available at this beach house.)brbrFlat screen TVs in All bedrooms. Kitchen is fully equipped. The upstairs unit is a 2/2 and the downstairs unit is a 2/1 and they each have separate entrances. Both units are rented together, NEVER separately.brbrThe upstairs has a king in the master and a king in the 2nd bedroom, plus a spacious kitchen and living room. The downstairs has a queen in one bedroom and 2 queen beds in the other room, plus a kitchenette.brbrPETS WELCOME with prior approval and pet fee.brbrVAC License # 24-0387br**No weddings or large events of any kind permitted**br***NO SMOKING****brYou must be 25 years or older to book this property.

*Charming Beach House directly ON the beach

Islamorada, Florida, United States

Bed

Bath