Vacation Rentals By Owner In Islamorada, FL

brBest side of the community for unobstructed view. Come enjoy relaxing or being active at luxurious Bay Harbour - a small and quiet gated community...perfect for a much needed get away! Bay Harbour is a small, quiet, private gated community with many amenities including large heated/cooled pool, hot tub/spa, tennis courts, pickle ball, clubhouse with large fitness center and gas grills located at the pool and clubhouse. Boat slip available for $150/week rent upon request. brbrThis beautiful newly remodeled home is located in Islamorada on Lower Matecumbe Key and brings you back to old Florida. Our home is a 3 bedroom, 2.5 bath that sleeps 6 people comfortably with a large living area and beautiful balcony with breath-taking views of the ocean and bay. Our home has been completely updated with new flooring, remodeled bathrooms, kitchen, plantation shutters, furniture, lighting, linens, and beautiful coastal decor and artwork. All bedrooms have king beds, and the unit also includes fast Wifi, new HD Smart TV’s, Fire TV with Live local channels, and Sonos speakers. Explore Islamorada with our 2 adult beach cruiser bikes and 2-person tandem kayak included for your enjoyment or just relax on the balcony watching the sunrise over the Atlantic Ocean while sipping a morning coffee, or enjoying a cocktail in the evening. This is the perfect place to spend your next vacation with family and friends while enjoying all of the amenities we have to offer. Tennis rackets and pickle ball paddles included. brbrThe screened balcony has plenty of seating and breath-taking views of both the ocean and inside bay on the quiets side of the marina. The balcony includes comfortable cushioned seating for relaxing and a dining table to enjoy a meal. The master bedroom has all new furniture (not pictured), king bed with a water view, plantation shutters, and access to the balcony. The second and third bedrooms also both have king beds, and plantation shutters. The living room and all bedrooms are equipped with brand new HD Smart TVs with access to Cable, Apple TV, Netflix, Amazon Prime Video and more. The gourmet kitchen has granite countertops, stainless steel appliances, a Nespresso expresso maker and is loaded with all of the cookware and utensils you need to feel right at home. The 3BR unit has an open floor plan (much larger than the 2BR), new flooring, and the dining room has comfortable seating all guests. The wet bar is loaded and even includes a margarita making ice blender. The condo has a full washer and dryer and all linens are new. There is also an additional freezer for bait and ice located in the kitchen.brbrBay Harbour is a small, quiet, private gated community with many amenities including large heated/cooled pool, jetted hot tub/spa, tennis courts, pickle ball, clubhouse with large fitness center and gas grills located at the pool and clubhouse.brbrIslamorada is conveniently located 90 minutes from Miami and Key West. During your visit you can feed the tarpon at Robbie's, enjoy a spectacular sunset at Morada Bay or swim with the dolphins at Theater of the Sea, and so much more!brbrIslamorada is the Sport Fishing Capital of the World” with tarpon, bonefish, permit, mahi-mahi, sailfish and swordfish in the waters surrounding Islamorada. There are many fishing charters are available nearby. Please inquire if you need a boat slip. Unfortunately, No trailers allowed to be kept on the premises.brbrWe have been visiting Islamorada for 25 years and we have compiled a list our favorite restaurants, reefs, and activities on the island. Whether you want to kayak, bike, fish, snorkel, dive or just sit by the pool or relax, our home has something for you!brbrbrWe prefer Saturday to Saturday rentals but contact us for exceptions in the off season.brRental Agreement and copy of Drivers License are necessary. brbr***Maximum 6 guests (ages 6 to adult), strictly enforced.***brVillage of Islamorada VACATION RENTAL LICENSE #: 26-4098brState of Florida License #CND5403693

Luxury 3 BR Remodeled! Ocean View PoolSpa, MarinaBikes Boat Slip Tennis/Pickle

Islamorada, Florida, United States

3

Bed

Bath

6

Sleeps

$371.32

brbrWelcome to our home away from home. White Marlin Beach, Waterfront property, quick access to the Bay from our canal. The best part is that you have access to our community private beach. You can kayak, swim, snorkel, fish, sun bathe and enjoy our beautiful Sunsets right from our beach. There are many things to do and many restaurant's to choose from. brEnjoy a peaceful stay at this lovely 2-bedroom house in Islamorada. This quaint property offers a cozy atmosphere that will make guests feel right at home. The bedrooms feature a comfortable king bed and a queen bed, ensuring a restful night's sleep. The bathroom is equipped with a hair dryer and a refreshing shower. In the additional living room space, there is a sofa bed for extra convenience. Stay connected with WiFi and take advantage of the washing machine and dryer to keep your clothes fresh. With AC throughout the house, you'll stay cool even on warm days. We look forward to hosting you at our place. You will definitely relax and make memories to last a lifetime.

Charming 2-bedroom house in enchanting Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$424.61

WATER FRONT CANAL HOME 3 BEDROOM/ 3 BATH HOME. brBRING YOUR BOAT, LOTS OF PROTECTED DOCKAGE. FULLY UPDATED HOME. HIGH SPEED WiFi and ALL SMART TVs. Coconut trees provide the shade to enjoy the calm breeze as you sit in one of our comfortable adirondack chairs and enjoy the tranquility.brUpdated Wi-Fi with new easy to connect AT&T modem. brDOCK RIGHT AT THE HOUSE! FISHING FUN RIGHT OFF DOCK!brGUEST BATHROOMS RENOVATED AND UPDATED! NICE PROTECTED DOCKAGE.brLOTS TO SEE AND DO CLOSE BY! MANY RESTAURANTS CLOSE BY!brWE MAKE COMMUNICATION EASY AND ALWAYS PROMPTLY RESPOND TO OUR GUESTS.brCLEANLINESS IS MORE IMPORTANT THAN EVER!brHOME IS CLEAN AND FRESH! INTERIOR RECENTLY PAINTED! brBRING YOUR OWN BOAT OR RENT ONE LOCALLY.brbrWEEKLY STAYS ARE WELCOME. LICENSE #VR-113. brbrCharming cozy private waterfront house on Atlantic side canal. brGreat protected dockage and room for your trailer. Newly paved, private road.brbrNew kitchen with all wood cabinets, granite counter tops and stainless appliances. The kitchen is fully equiped with all the essentials.brbrThree bedrooms and three bathrooms. Downstairs bedroom has full bathroom with shower and is separate from upstairs and opens to carport. Home is perfect for four adult plus two kids.brbrWe have lots of great dockage for your boat. The large dock/seawall area extends 90 feet and includes a nice cut-in slip. The dock includes electric, water. There is also a cleaning station on the dock. Also there is plenty of room for trailers on the side of the home. It's all about the boating. brbrThere are several local boat ramp options close by. brbrKeep in mind that trip insurance is available and is recommended.brThere are many options including through VRBO or other mainstream recognizable third party providers.brBe sure to understand the coverage, benefits and limitation of any policy you purchase.brbrbrINSPECTED, PERMITTED & LICENSED BY THE VILLIAGE OF ISLAMORADA # VR-113.brbrKeywords: License #VR-113, Islamorada Florida, Lower Matecumbe, Dockage, Waterfront, WiFi, Internet, clean, Tropical, Home, waterfront, deep dockage, bungalow, shopping, dinning, beach, kayak, scuba, snorkeling, lobsterbrfishing, dock, boat, ocean, bay, Keys, key, Islamorada, Upper Keys, Lower Matecumbe, kitchen, open, clean, bright, comfortable, private, protected, deep water, boating, swimming,! Amazing

CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1884.12

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, tiki hut on private beach, heated pool and wireless remote Internet. Southern Diversion pool and patio area has just been completely renovated with marble decks.brbrIslamorada is located one hour and 1/2 south of South Beach and two hours north of Key West. This spectacular oceanfront estate features 5 bedrooms, 3.5 baths. Bedroom One: king bed, Bedroom Two: 1King bed , Bedroom Three: 1 King bed, Bedroom Four: 1 bunk-bed with a pull-out trundle and 2 twin beds, Bedroom 5: 2 sets of bunk beds with trundle. Bottom bunk on one bed is a double. Brand new flat screens in every room.We provide a full time property manager available 24/7 for anything our guests may need. Southern Diversion offers the perfect escape and tropical dream vacation. Occupancy is 2 adults per room. Children 6 and older are considered adults. Under 6 not included in occupancy count.brbrIslamorada The Sport Fishing Capital of the World hosts an array of activities from relaxing on our private beach to world class scuba diving. From our private beach you can go catch fresh Florida lobster, Go shelling, Reef snorkeling off Cheeca Rock Reef, See live coral reefs and catch Bonefish. Southern Diversion is located directly in the Village of Islamorada (Mile Marker 82) which means you are within 5 minutes of the best cuisine Islamorada has to offer. Robbie's of Islamorada (5 min car ride) offers many different marine activities including boat rentals, jet skiing, kayak's and a delicious restaurant. Don't forget to visit Scarface in the Tarpon Feeding area. Also at Robbie's they will cook your fresh catch at the Hungry Tarpon Restaurant. If you are in the mood for a nice stroll, Bentleys Restaurant is right outside our gate or you can walk to Morada Bay where you can enjoy a relaxed beach atmosphere.brFeel free to visit other Southern Diversion Properties in The Florida Keys brhomeaway 7396601 brhomeaway 3577977brKeywords: Estate HomebrLicense No. VR 26-0394

Southern Diversion Estate Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$211.87

Coral Harbor is the best kept secret in Islamorada. Quiet, gated community with ocean views, clubhouse, pool and a saltwater lagoon with beach. Minutes from all the best restaurants; both casual and fine dining. Great marinas, movie theater, Founders Park and 2 large grocery stores are all minutes away. brbrThis spacious, 2/2 recently updated condo has a fully stocked kitchen and large rooms with plenty of closet space. Unit has a comfortable screened balcony overlooking the lagoon with ocean views that are perfect for your morning coffee or a sunset drink. Assigned covered parking spot is very convenient.brbr**Must reserve 30 days in advance for required Association approval.**

A Great Place! Spacious 2/2 retreat with ocean views in the heart of the Keys.

Islamorada, Florida, United States

Bed

Bath

6

Sleeps

$663.3

Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine when you think of a laid-back Keys escape. Surrounded by lush, tropical landscaping and offering total privacy, this 3-bedroom, 3.5-bath getaway has all the extras—100 feet of dockage, a heated pool and spa, and even two paddleboards ready for your adventures.brbrInside, the home is bright, spacious, and tastefully done with a clean coastal feel. Each bedroom has its own en-suite bath, making it perfect for couples or families traveling together. The kitchen is fully stocked, the living spaces are comfortable and welcoming, and there's plenty of room to spread out—both inside and out.brbrOut back, you'll find your own private oasis. Lounge by the pool, take a dip in the spa, fire up the grill, or launch the paddleboards for a peaceful cruise down the canal. The 100' dock has room for your boat and quick access to the ocean—ideal for fishing, sandbar days, or sunset cruises.brbrClose to local restaurants, marinas, and some of the best spots in the Keys—but just far enough away to feel like your own private hideaway.brbrYour slice of Islamorada paradise awaits.

Discover luxury at Stillwater Cove, a stunning 3BR retreat with beautiful pool and dockage.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$248.51

A fully furnished two bedroom, two bath townhouse located in Islamorada, also known as the Fishing Capital of the World. All amenities needed in order to enjoy a relaxing vacation. The property has a swimming pool, tennis court, pickleball court, shuffleboard, boat ramp and dock space for a boat up to 25' as stated in boat registration. brbrIf bringing a boat or renting one during you stay, proof of insurance with liability limits as well as boat registration is mandatory and should be sent to owner prior to your arrival. Use of dock space is on a first come, first serve basis with owners having priorities. Dock or ramp will not be allowed to be used until insurance and registration documents are provided to our dock master.brbrMaster bedroom is located on the third floor and has king size bed, its own private bathroom and screened porch. Second bedroom is on second floor and has queen size bed. A queen size air mattress is also available.brbrThere is a living room, dining room, second full bath and a fully equipped kitchen, as well as a large screened porch overlooking the pool and tennis court.brbrFull size washer and dryer are located in the garage. Also, a covered carport and ample parking for vehicle. Barbecue grill is stored in garage.brbrWiFi internet, televisions in both bedrooms and living room, including blue ray and DVD player.

A little Piece of Heaven to wash your worries away

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1221.1

Welcome to Alligator Reef Estate, a gated oceanfront property in Islamorada offering two homes on one beautiful waterfront parcel—perfect for larger families or groups looking to enjoy the Florida Keys together while still having their own space.brThe estate includes the Conch Home, a 3 bedroom, 2 bathroom home featuring a private fenced heated and chilled pool, outdoor kitchen and bar area, ping pong table, and bicycles for exploring the area. Just in front of it sits the Lobster Home, a comfortable 2 bedroom, 2 bathroom home that provides additional space for guests.brTogether, the property offers 5 bedrooms and 4 bathrooms, making it ideal for group vacations, family gatherings, or multiple families traveling together.brBoth homes share the beautiful oceanfront grounds which include a sandy lounging area, fire pit, observation dock, and kayaks and paddleboards for enjoying the clear waters of the Keys. Whether you're relaxing by the pool, gathering around the fire pit at sunset, or launching a paddleboard from the shore, there's something here for everyone.brAlligator Reef Estate offers the perfect balance of privacy, space, and true island living—creating a one-of-a-kind Florida Keys getaway right on the ocean. brVACATION RENTAL LICENSE: 24-0389 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.brbrIf 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.

Spacious 5BR home in Islamorada, perfect for 14 guests with ocean views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$515.95

Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port Antigua is one of the best neighborhoods in Islamorada. Not only does it offer a private beach, but also has a private boat ramp right inside the neighborhood. With great fishing access to the bay and open ocean just through channel 5 or channel 2. Lots of amenities and restaurants in the area to list but will provide information at the property. On the second floor there is a Master Bedroom with an on-suite bathroom. Guest/2nd Room is also located on the second floor with a full bathroom right outside the door in the hallway. Full size frontload Washer & Dryer which are also located on the second floor. Kitchen and living room are also located on the second floor. In the third floor you have a second master bedroom with an on-suite bathroom and a walk in closet. Kitchen is fully equipped for all your cooking needs. There is a total of 75 feet of dock, but a boat on a lift which will remain on the property unless you need the entire dock, then an additional fee will be applied. Please inquire before reserving if additional dock space is necessary. For more information please conact me at Agueracarlos@gmail.com. Thank you!

Paradise Retreat

Islamorada, Florida, United States

Bed

Bath

Sleeps

$557.46

Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete with tennis courts, pickleball court, weight room, pool, dockage, fish cleaning station, Smart TV's for streaming (no cable) and Wi-Fi. The condo boasts some amazing views of the Clear Blue waters of the Atlantic Ocean looking over Sea Oats Beach. Relax on your own private roof top patio and enjoy a beautiful sunrise of the glow of a famous Florida Keys Sunset. brNOTE: Onsite trailer parking is not allowed at Bay Harbour community. brVACATION RENTAL LICENSE: 24-0309 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.

Enjoy stunning views at Bay Harbour C-312, a 3BR condo in picturesque Islamorada.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$316.94

Welcome to 128 Tequesta Street, a charming three-bedroom, two-bath waterfront home designed for the perfect Florida Keys vacation. Located on a canal in Plantation Key, the home offers convenient dockage so you can bring your boat and enjoy easy access to the beautiful waters of Florida Bay.brbrThe outdoor space is where this home truly shines. Relax by the pool, gather with friends under the tiki hut, or mix up a drink at the outdoor bar while enjoying the warm Keys breeze. For a little adventure, hop in one of the kayaks and paddle your way out to Florida Bay.brbrInside, the home features a comfortable open-concept layout that works perfectly for families and entertaining. The kitchen includes bar seating and flows easily into the living area, creating a welcoming space to cook, relax, and spend time together after a day on the water.brbrWhen you're ready to explore, you're just minutes from Plantation Key and the best of Islamorada — including great restaurants, local shops, marinas, and grocery stores.brbrWhether you're boating, relaxing poolside, or exploring the Keys, 128 Tequesta Street is the perfect place to experience the laid-back island lifestyle.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.

Charming 3-Bed, 2-Bath Canal Home in Tavernier, FL, with Private Pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$338.1

Large 3/2 with ground level carport. Lagoon side screened porch 50' x 10'. Terrace on Ocean side is open. Boat access on Gulf side fishing and snorkeling, you can be in the ocean quickly. WiFi internet, 5 large screen TVs all with internet access. Spectacular view, great diving locations and fishing.

Ocean View with protected dock on lagoon with private boat ramp

Islamorada, Florida, United States

Bed

Bath

Sleeps

$399.57

Escape to your own slice of paradise in this beautiful canal-front vacation home in Tavernier. This spacious property offers the perfect setup for families or groups traveling together.brUpstairs features a 3-bedroom, 2-bathroom home with comfortable living spaces and everything you need for a relaxing stay. Downstairs, a separate 1-bedroom, 1-bath apartment provides additional privacy, making it ideal for extended family or friends traveling together.brThe outdoor space is designed for relaxing and entertaining. The private pool is located in the front of the home and the property is gated, creating a very private setting to enjoy the Florida Keys sunshine. Pool is heated by request at an additional charge. In the backyard, you'll find a tiki hut, outdoor kitchen with bar seating, and a large TV, perfect for grilling fresh seafood, watching the game, or enjoying evening cocktails.brBoaters will appreciate the canal-front location with dockage and two boat lifts, making it easy to bring your boat and explore the beautiful waters of the Florida Keys right from your doorstep.brWhether you're lounging by the pool, entertaining under the tiki hut, or heading out for a day on the water, this Tavernier home offers the perfect blend of comfort, privacy, and classic Keys living.brAlso note, this beautiful home is available for monthly rentals only.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 spacious 4-bedroom canal home in beautiful Islamorada!

Islamorada, Florida, United States

4

Bed

3

Bath

8

Sleeps

$509.63

This listing is for a room within a hotel.brbr✦ Your room is 370 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Outdoor shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Hotel

Fun Under the Sun! Beachfront, w/ Pool Onsite, Free Parking | Pets Allowed

Islamorada, Florida, United States

Bed

Bath

Sleeps

$303.24

Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features two private bedrooms, a fully stocked kitchen, and a spacious living area that comfortably accommodates up to four guests. brbrbrbrThere are many sights to see and activities to enjoy nearby. Within just a mile from our cottage is Islamorada's top-rated attraction, Robbie's Marina, where you can embark on a variety of adventurous activities, including snorkeling, fishing, parasailing, or sunset charters, as well as guided tours by kayak or paddleboard through the mangrove channels encompassing the island's coasts. During your time on the water, you may encounter fascinating marine species, such as manatees, Atlantic bottlenose dolphins, and sea turtles. From the shore at Robbie's Marina, try hand-feeding the massive tarpon and friendly nurse shark species commonly found in our warm, tropical waters. brbrbrbrThere's something to please every family member here in the Florida Keys, such as swimming with dolphins and sea lions at Theater of the Sea or learning more about the island's culture and history at the History of Diving Museum. Foodies will also enjoy a range of restaurants serving various dishes, including authentic Cuban and Florida Keys cuisine. Our favorites include Midway CafÃ© for delectable breakfasts, baked goods, smoothies, and the best Key Lime Pie FrappÃ©! For dinner, consider reserving a table at Lazy Day's, where you can enjoy a superb ocean view from the comfort of their dining room and an excellent menu selection that will appeal to even the pickiest palettes. brbrbrbrAfter a fun-filled day traversing the island chain, return home to the comfort of your private vacation home, where you can rest easy and recharge. To help you relax, consider a dip in the communal, heated swimming pool, which is exclusively accessible to the few cottage homes at Shady Palms. Are you planning on doing some boating Caloosa Cove Marina is just 3 miles south and offers competitive wet slip, trailer storage, and fuel prices.

Cottage

2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool

Islamorada, Florida, United States

Bed

1

Bath

4

Sleeps

$1836.16

Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamorada - observation dock for paddle boarding, fishing and kayaking. Property is flanked by natural preserve on one side and has wide open expansive ocean views. The private beach is located along a wildlife protected turtle nesting beach that left natural for turtle nesting season. brbrThere is an incredible 180 degree water view from almost every room in the house. Spectacular sunrises flood the rooms with golden light reflected off the ocean. The sun rises over the water every morning within your view. The sunsets are equally stunning over the peninsula leaving the view with purple and pink clouds. Constant onshore breeze drifts through the house with pure, invigorating ocean scents. brbr2 Paddle boards and 2 kayaks are included with rental as the waters off the house are perfect for exploring by kayak. 2 cabanas for rest and relaxation - one by the pool and one the dock. The wildlife is stunning and you are bound to see amazing creatures during each outing! There is also an amazing State Park (an island) just a paddle away. Alligator Reef Lighthouse is on the horizon and the ocean views from the end of the observation dock are simply incredible. The oceanfront pool is heated to 86 degrees.brbrThe house is a 100% non-smoking property. The observation dock is for non-motorized vessels only as the tides can get very low during full moons.brbrTHIS PROPERTY RENTS SATURDAY TO SATURDAY brRobbie's of Islamorada is down the street from the property a half mile and offering an outdoor restaurant, jet ski rentals, tarpon feeding, shops, fishing charters, snorkeling trips & sunset cruises to the Lighthouse.brbrAbout the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel and is exceptionally clean and easy to enjoy.brbrWe privately own a total of 5 boutique vacation rentals in Islamorada:brVRBO listing #1576833 (5 bedroom)brVRBO listing #1054019 (5 bedroom)brVRBO listing #1977457 (7 bedroom)brVRBO listing #689629 (5 bedroom)brbr (no boat dockage due to tides)brbrLICENSE #: 26-0279 - Islamorada

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Islamorada, Florida, United States

Bed

Bath

Sleeps

$556.93

brbrThe Garden View Cottage is a charming two-bedroom, one-bath cottage nestled in the center of Mermaid's Bay Boutique Estate—a private 3.5-acre waterfront retreat in the heart of downtown Islamorada. The estate features 300' of bayfrontage, a pool and hot tub, protected boat basin and more. brbr brbr• Resort-style shared amenities, including heated pool and spa br• Sandy beach with hammocks, lounge chairs, and tiki hut br• Protected boat basin with small rampbr• Complimentary kayaks, paddle boards, and bikes br• Two private porches, one screened br• Private grill and parking spacebrbr brbr2 Bedroomsbr• Primary Bedroom: King Bedbr• Guest Bedroom: 2 Queen Bedsbrbr1 Bathroombr• Shared full bath with walk-in shower brbrLiving Areabr• Comfortable kitchen, butler's pantry, dining area and living roombr• Thoughtfully stocked kitchen with full-size appliancesbr• French doors fill the space with soft, natural lightbrbrIn-Home Amenitiesbr • Washer/dryerbr • Filtered water dispenserbr • Smart TVs and high-speed Wi-Fibr • Starter supplies provided, including toiletries and paper goodsbrbr brbrThe protected boat basin can accommodate boats of all sizes, providing direct access to the Florida Bay. Dockage and trailer storage is included with the stay. brbr brbrLocated in the heart of downtown Islamorada, within easy walking distance of popular restaurants, breweries, and local shops.brbr brbrRentals are from Friday to Friday. Differing dates may be approved on a case-by-case basis.brbrThis property is locally managed by Solace Properties. Once your booking is confirmed, you'll receive a rental agreement via email to review and sign. Rental payments are processed directly through Solace Properties, while VRBO collects their service fee separately. For any questions or assistance, Solace Properties will be your main point of contact.

Cottage

Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More

Islamorada, Florida, United States

Bed

Bath

Sleeps

$878.1

brbrThe Bay View Cottage is a charming two-bedroom, one-bath cottage tucked beneath the shade of mature trees along the bayfront at Mermaid's Bay Boutique Estate—a private 3.5-acre waterfront retreat in the heart of downtown Islamorada. With peaceful views of the Florida Bay and a shaded front porch that stays cool throughout the day, this cozy cottage offers a quiet island escape while keeping you close to Islamorada's best dining, shopping, and recreation.brbr brbr• Resort-style shared amenities, including heated pool and spa br• Sandy beach with hammocks, lounge chairs, and tiki hut br• Protected boat basin with small rampbr• Complimentary kayaks, paddle boards, and bikes br• Shaded front porch with comfortable seating and water views br• Private grill and parking spacebrbr brbr2 Bedroomsbr• Primary Bedroom: King Bedbr• Guest Bedroom: 2 Queen Bedsbrbr1 Bathroombr• Shared full bath with walk-in shower brbrLiving Areabr• Open-concept living and dining area with bay viewsbr• Thoughtfully stocked kitchen with full-size appliancesbr• French doors fill the space with soft, natural lightbrbrIn-Home Amenitiesbr • Washer and dryerbr • Filtered water dispenserbr • Smart TVs and high-speed Wi-Fibr • Starter supplies provided, including toiletries and paper goodsbrbr brbrThe protected boat basin can accommodate boats of all sizes, providing direct access to the Florida Bay. Dockage and trailer storage is included with the stay. brbr brbrLocated in the heart of downtown Islamorada, within easy walking distance of popular restaurants, breweries, and local shops.brbr brbrRentals are from Friday to Friday. Differing dates may be approved on a case-by-case basis.brbrThis property is locally managed by Solace Properties. Once your booking is confirmed, you'll receive a rental agreement via email to review and sign. Rental payments are processed directly through Solace Properties, while VRBO collects their service fee separately. For any questions or assistance, Solace Properties will be your main point of contact.

Cottage

Charming Bayfront Cottage in Heart of Islamorada with Heated Pool, Deep Dockage, Kayaks & More

Islamorada, Florida, United States

Bed

1

Bath

6

Sleeps

$293.52

brbrTime Well Wasted is an inviting three-bedroom retreat located in the Port Antigua neighborhood of Lower Matecumbe Key. A highlight of every stay is access to the private bayfront homeowners' beach—a peaceful stretch of sand along the Florida Bay with tiki huts, calm shallow water, and space to relax under the sun.brbr brbr• Access to private homeowners' beachbr• Dockage for boats up to 20 ft (quick access to Florida Bay)br• Use of neighborhood boat rampbr• Kayaks and paddle boards provided for guest usebr• Spacious covered porch with seating, grill, and golden-hour viewsbrbr brbr3 Bedroomsbr• Primary Suite: King bedbr• Guest Bedroom 1: Queen bedbr• Guest Bedroom 2: Two queen bedsbrbr2.5 Bathroomsbr• Master ensuite bathroombr• Jack-and-Jill shared bath between guest rooms (each with private vanity and toilet)brbrLiving Areasbr• Open living and dining areabr• Fully equipped kitchenbr• Large covered porch for outdoor grilling and loungingbrbr brbrLocated just minutes from the Florida Bay. Enjoy quick, easy access to world-class backcountry fishing on your skiff, or explore the calm waters by kayak or paddle board.brbr brbrPort Antigua is a quiet, upscale neighborhood on Lower Matecumbe Key—just a short drive from downtown Islamorada's restaurants, marinas, and shops.brbr brbrFor the safety and security of our guests and the property, this home is equipped with exterior security cameras. These are located outside the home only and do not record audio.brbrThis property is locally managed by Solace Properties. Once your booking is confirmed, you'll receive a rental agreement via email to review and sign. Rental payments are processed directly through Solace Properties, while VRBO collects their service fee separately. For any questions or assistance, Solace Properties will be your main point of contact.

Peaceful Home with Skiff Dockage + Access to Private Bayfront Beach

Islamorada, Florida, United States

3

Bed