Islamorada Rentals
- From $315 per night (USD)
VRBO
3 bed 2 bath condo at Futura Yacht Club!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Completely remodeled 3 bedroom condo. Kitchen completely redone Spring of 2021 Sleeping accommodations: king bed in mas ...
From $315 per night (USD)VRBO
- From $1248 per night (USD)
VRBO
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
82754 Overseas Highway - OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Ke ...
From $1248 per night (USD)VRBO
- From $119 per night (USD)
VRBO
Port of Call C2 - Townhome with Oceanview
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Port of Call C-2 - Charming two bedroom, two and a half baths condo with ocean views, a sunroom for a dining room, and n ...
From $119 per night (USD)VRBO
- From $228 per night (USD)
VRBO
Beautiful Cottage in Islamorada on canal front! Wifi, Smart TVs and No Stairs!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated and decorated CBS home on bay side with charming details throughout. Wifi, smart TV and no stairs! ...
From $228 per night (USD)VRBO
- From $521 per night (USD)
VRBO
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
COVID-19 Update: Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manag ...
From $521 per night (USD)VRBO
- From $564 per night (USD)
VRBO
COASTAL ELEGANCE FOR RENT IN ISLAMORADA !!! PARADISE FOUND ON DEEP WATER
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This designer REMODELED IN JULY 2021 3bdr, 2bath home is located on a 60 foot deep water dock in quiet Plantation Key, F ...
From $564 per night (USD)VRBO
- From $886 per night (USD)
VRBO
Sanctuary In Paradise Featured On H G T V
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Open Ocean on “Millionaire’s Row” Unique property featuring separate: ~1BR 1BA Upstairs Suite ~2BR 2BA Downstairs Apt. ...
From $886 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Relax in Islamorada-Canal Front 3 Bedroom \/ 2 Bath Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax in Islamorada Canal Front 3 Bedroom/2 Bath Home Spacious Keys style 3 bedroom / 2 bath home located on deep cana ...
From $475 per night (USD)VRBO
- From $280 per night (USD)
VRBO
WATERFRONT KEYS COTTAGE GREAT RATES ! Walking distance to world famous Lorelei
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
1940s Keys Cottage with *dockage available. Waterfront and walking distance to world famous Lorelei Cabana Bar & Restaur ...
From $280 per night (USD)VRBO
- From $193 per night (USD)
VRBO
Beautifully Renovated 2 Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 ...
From $193 per night (USD)VRBO
- From $654 per night (USD)
VRBO
Manatee Harbor - Bayfront Home on Plantation Key
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Manatee Harbor ~ Where bayside paradise awaits you! This 4 bedroom home is nestled along the bay in one of ...
From $654 per night (USD)VRBO
- From $1575 per night (USD)
VRBO
4 bedroom, Ocean front,Top tier Condo in Islamorada, Florida Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Maison Residences Unit 204, Poolside... — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS — A world- ...
From $1575 per night (USD)VRBO
- From $210 per night (USD)
VRBO
Plantation Key Colony Canal with Boat lift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Canal side Retreat in the Colony 28 day minimum no pets! You won't believe your eyes! It looks like a cozy conch cottag ...
From $210 per night (USD)VRBO
- From $374 per night (USD)
VRBO
Ocean Views for DAYS!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
132 Columbus Drive - Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in t ...
From $374 per night (USD)VRBO
- From $562 per night (USD)
VRBO
THE premier gated oceanfront complex in the heart of Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
May and June 2024 Special $3400 weekly!!....Oceanfront Maison Matecumbe #303 - Maison Matecumbe is a premier gated ocean ...
From $562 per night (USD)VRBO
- From $470 per night (USD)
VRBO
Paradise Found - Three Story Beach House w\/ private beach, dock and Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
3 story bayside home with its own beach. Great location. Private residential area, yet close to Everything. Due to u ...
From $470 per night (USD)VRBO
- From $819 per night (USD)
VRBO
Luxury villa with beautiful bay views | Pool | Little Basin Villas | Bay Villa 9
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Villa #9 is part of Little Basin Villas upscale community of nine luxury vacation villas located in the heart of the ...
From $819 per night (USD)VRBO
- From $402 per night (USD)
VRBO
Family\/Pet Friendly Venetian Shores Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful Venetian Shores pool home with plenty of space to relax and play. Situated on a deep water canal with qui ...
From $402 per night (USD)VRBO
- From $467 per night (USD)
VRBO
San Remo Canal Front
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
San Remo Canalfront - Venetian Shores five bedroom and four bath home with 70 ft. dock just minutes to Snake Creek for i ...
From $467 per night (USD)VRBO
- Click For Pricing
VRBO
Venetian Shores Pool Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenie ...
Click For PricingVRBO
- From $239 per night (USD)
VRBO
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches ...
From $239 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Pineapple Point pet friendly paradise Islamorada\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Pineapple Point, where the quiet peaceful setting will entice you to relax and enjoy Keys living. Our 2 bedro ...
From $150 per night (USD)VRBO
- From $292 per night (USD)
VRBO
Islamorada 3\/2 condo. Dockage, swimming pool, sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit c ...
From $292 per night (USD)VRBO
- From $292 per night (USD)
VRBO
Just a Few Friends - Ocean View and Bring your Boat!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in ...
From $292 per night (USD)VRBO
- From $929 per night (USD)
VRBO
Waterfront Oasis Legal weekly rental*Mins2Beach*Tons of dockage
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
I am a legal weekly rental in Islamorada!!! Commercial Ice Machine, bait freezer, and fish cleaning station!! SUPER PRI ...
From $929 per night (USD)VRBO
- From $821 per night (USD)
Expedia
BAYSIDE PARADISE ~ Heart of Islamorada ~ Private Boat Dockage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into ou ...
From $821 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Indian Mound - Islamorada Keys Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Indian Mound is the ultimate family getaway! Relax in this three bedroom / two bathroom home that has recently been fur ...
From $175 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Beautiful Bayfront Home with Amazing Sunsets
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Property has a large kitchen and living area open to amazing views of the bay with 4 bedrooms and 3 full baths. Yo ...
From $700 per night (USD)VRBO
- From $514 per night (USD)
VRBO
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Home has been completely renova ...
From $514 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Super Penthouse - Futura Yacht Club #603
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Top Floor Penthouse Condo. -Air Conditioning -Stainless Steel appliances. -Granite countertops throughout. -2 Samsung ...
From $400 per night (USD)VRBO
- From $237 per night (USD)
VRBO
Discover the Charm of Island Living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf o ...
From $237 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Executive Bay Club Condo (2 bds + loft & 3 full baths)
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 9
Come stay and watch the sunsets at our beautifully updated Keys townhouse at Executive Bay Club located in Islamorada on ...
From $175 per night (USD)VRBO
- From $308 per night (USD)
VRBO
Beautiful 'Keysey' Condo in Gated Community 24-0169
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the spirit of the Florida Keys in this 'keysey' furnished condo with everything provided. All you have to do is s ...
From $308 per night (USD)VRBO
- From $339 per night (USD)
VRBO
Islamorada Luxury Waterfront Condo with Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in ...
From $339 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much mor ...
From $315 per night (USD)VRBO
- From $373 per night (USD)
VRBO
Unique 2 Bedroom Bay Front Home with Roof Top Terrace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
75130 Overseas Highway - Great house in Lower Matecumbe (south side of Islamorada) at the 75-mile marker on the bayside. ...
From $373 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Quiet Home Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+2 Kayaks+2 Offices
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Still available Feb 2024 You will see amazing sunsets in our community sandy beach, fish or relax on pier, dip in the he ...
From $295 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Renovated canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! A tropical palmy dream and playground for ocean lovers. Minutes on boat from the best san ...
From $700 per night (USD)VRBO
- From $575 per night (USD)
VRBO
Beautiful New Island Home for 2 Small Families
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Plan your vacation getaway in paradise at this amazing new canal-front home with all the comforts of home in a quiet nei ...
From $575 per night (USD)VRBO
- From $215 per night (USD)
VRBO
Tropical Paradise at Futura Yacht Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Futura Yacht Club is a private 70 unit community with a 53 slip marina. Easy access to the ocean through Snake Creek or ...
From $215 per night (USD)VRBO
- From $477 per night (USD)
VRBO
Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete ...
From $477 per night (USD)VRBO
- From $573 per night (USD)
VRBO
☀️Luxury 3 BR Remodeled! Ocean View, Pool Spa, Marina Bikes Kayak Tennis\/Pickle
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy relaxing or being active at luxurious Bay Harbour - a small and quiet gated community...perfect for a much ne ...
From $573 per night (USD)VRBO
- From $198 per night (USD)
VRBO
Canal front Oasis with Pool and Tiki Hut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
128 Tequesta Street - The perfect vacation home! This charming three-bedroom two bath home has everything you need for t ...
From $198 per night (USD)VRBO
- From $1000 per night (USD)
VRBO
Seaside Sanctuary 5 bed, 5 bath pool home
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featurin ...
From $1000 per night (USD)VRBO
- From $496 per night (USD)
VRBO
Cute Canal front Venetian Shores Weekly Rental!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
107 San Remo Drive - Comfortable Venetian Shores canal home that has two-bedroom one bath upstairs and a one bedroom one ...
From $496 per night (USD)VRBO
- From $198 per night (USD)
VRBO
Bay Views from this Charming 3 Bedroom Canal Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
186 Airstream Lane - Located on a quiet street in Islamorada, this home offers you the best of both worlds. Fantastic, p ...
From $198 per night (USD)VRBO
- From $469 per night (USD)
VRBO
Panoramic Ocean Views from this 3 Bedroom Islamorada Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
137 LeSerra Lane - Beautiful designer appointed Oceanside canal home located at the mile marker 76.5 in Lower Matecumbe ...
From $469 per night (USD)VRBO
- Click For Pricing
Expedia
Island Dreams: Islamorada Studio
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Nestled in the stunning Islamorada, Florida Keys, this modernized oceanfront Studio Suite boasts a queen-size bed, and t ...
Click For PricingExpedia
- From $318 per night (USD)
VRBO
Seaside Splendor: Heart of Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 6
Experience the charm of the Studio Suite, a spacious single room featuring a comfortable queen-size bed and a twin sleep ...
From $318 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Vibrant Islamorada Studio Queen Bed, Balcony, Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 3
Experience the charm of the Studio Suite, a spacious single room featuring a comfortable queen-size bed and a twin sleep ...
From $350 per night (USD)Expedia
- From $382 per night (USD)
VRBO
Embrace the Sugar Rush Experience! Courtyard View, Free Parking, Onsite Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $382 per night (USD)VRBO
- From $411 per night (USD)
VRBO
Best Place to Unwind! Oceanfront, Pets Allowed, Onsite Pool, Near Anne's Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $411 per night (USD)VRBO
- From $355 per night (USD)
VRBO
Ideal Mix of Comfort and Value! Free Parking, Onsite Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $355 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Large Screened Porch, Professional Cleaning, Wifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Oceanfront 90 mm Plantation Key , full screened in terrace 6.5 ft by 28.5 ft. Newly decorated white tile & Berber carp ...
From $250 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Best location in downtown Islamorada. Beach access and boat trailer parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. Close enough to walk a ...
From $225 per night (USD)VRBO
- Click For Pricing
VRBO
Islamorada Getaway in exclusive Port Antigua. Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the beautiful Florida Keys in an exclusive neighborhood. Wake up to the sunrise with coffee and breakfast on t ...
Click For PricingVRBO
- From $473 per night (USD)
VRBO
The Turtle Nest | Pet Friendly! \"Venetian Shores\"
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Beautiful home with pool is nestled in the quiet neighborhood of Venetian Shores Islamorada. It sits right on a ...
From $473 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Keys Villa--Islamorada private beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom "gem" in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, ...
From $400 per night (USD)Expedia
- Click For Pricing
VRBO
Stunning Penthouse 3 bedroom Apartment, New
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Stunning 3 bedroom Penthouse is absolutely stunning! The photos do not due justice to the amazing ceiling, Livingro ...
Click For PricingVRBO
- From $719 per night (USD)
VRBO
Enjoy a Hassle-Free Stay! 2 Convenient Units, Free Parking, Onsite Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $719 per night (USD)VRBO
- From $719 per night (USD)
VRBO
Enjoy a Hassle-Free and Suiting Stay! 2 Family-friendly Units, Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Inspired by the lush tropical surroundings of Islamorada, our fully-equipped resort rooms feature premium bedding and ge ...
From $719 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Paradise in the Keys with Sandy Beach, Heated Pool, Fishing Pier, and 2 Kayaks\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Getaway to the warm Florida Keys in our slice of paradise. Unwind in our 2-bedroom, 2-bathroom townhome. You will enjoy ...
From $180 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Islamorada Oasis, Luxury open concept private home.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Islamorada Oasis is designed for families and outdoor lovers! Inside and out, its ready for entertaining and keys styl ...
From $500 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Fantastic Bayside Townhouse
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Fantastic gated Bayside townhouse with all the bells and whistles. Excellant location with everything you need to have a ...
From $395 per night (USD)VRBO
- From $464 per night (USD)
VRBO
Villa Morada ~ Relaxed Luxury 4 Bedroom Islamorada Home with Pool & Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully updated 4 bedroom and 2.5 bath resort-like home is nestled in one of Plantation Keys most desirable nei ...
From $464 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Best Location in Islamorada!! Beach access - Boat trailer parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Gorgeous and highly appointed luxury Island villa with beach access. You are right in the middle of it all with this per ...
From $225 per night (USD)Expedia
- From $490 per night (USD)
VRBO
SALT HAVEN - BEAUTIFUL & CLEAN 70' WATERFRONT\/CANAL POOL HOME + PRIVATE BEACH
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The Salt Haven is a beautiful canal front, pool home in Port Antigua ready for your vacation get away. Port Antigua is o ...
From $490 per night (USD)VRBO
- Click For Pricing
Expedia
FLORIDA KEYS
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
ONLY WEEK AVAILABLE: OCTOBER 5-12, 2024. Caloosa Cove Resort and Marina is located on 10 tropical acres in Islamorada, F ...
Click For PricingExpedia
- From $254 per night (USD)
VRBO
Canal-front home with private dock, wraparound deck, & central AC - snowbirds OK
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Plaza Del Sol Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $254 per night (USD)VRBO
- From $302 per night (USD)
Expedia
Deep Water Canal Home with Private Pool and Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
PROPERTY NAME: Manatee Manor 141 Tequesta St., Tavernier, Florida LOCATION: Bayside canal home located on a deep wide c ...
From $302 per night (USD)Expedia
- Click For Pricing
VRBO
Ocean Breeze. Oceanfront Resort Style Condo in the Florida Keys (Islamorada)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Oceanfront resort style condo in the Florida Keys (waterfront) Over1,700 square feet with screened in porch for amazing ...
Click For PricingVRBO
- From $268 per night (USD)
Expedia
Beautiful Lower Unit with Dockage, Pool and Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
PROPERTY NAME: Parrot Eyes 130 Plantation Ave. Tavernier, Florida 33070 LOCATION: Bayside Canal home located in Taverni ...
From $268 per night (USD)Expedia
- From $278 per night (USD)
VRBO
Treasure Harbor Hideaway | Luxury Waterfront
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your personal paradise | Monthly Rates! - a deluxe Keys retreat that promises to take your coastal living exp ...
From $278 per night (USD)VRBO
- Click For Pricing
Expedia
Sensational remodeled single family home with pool, hot tub and tiki bar.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
PROPERTY NAME: Plantation Adventure 120 Plantation Drive, Plantation Key, FL LOCATION: Oceanside House on the canal MI ...
Click For PricingExpedia
- From $429 per night (USD)
VRBO
Remodeled Stilt home with Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PROPERTY NAME: Blue Water Retreat 137 Ocean Lane, Islamorada, Florida LOCATION: Oceanside Canal home located in Lower M ...
From $429 per night (USD)VRBO
- From $7632 per night (USD)
VRBO
Island Beach House Oasis-Your Memory Maker awaits.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
There is luxury, luxury and unrivaled, and then there is the Bay front Island Beach House Oasis that offers that and mor ...
From $7632 per night (USD)VRBO
- From $636 per night (USD)
VRBO
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
About this space Relax in Islamorada with a beautiful private beach. Enjoy the day deep sea fishing and end up watching ...
From $636 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
Bayfront paradise in Islamorada, FL.
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
This stunning residence in Islamorada offers breathtaking views and luxurious amenities, ideal for serene living. Each b ...
From $1500 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Sunny Escape! Spacious Oceanfront Suite with Balcony! Beachfront Resort w\/ Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and pl ...
From $375 per night (USD)VRBO
- From $1001 per night (USD)
VRBO
Seaside Sanctuary in the Heart of Islamorada
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled between the Cheeca Lodge and Caribbean Resort, discover our exclusive 4-bedroom oceanside sanctuary, delivering ...
From $1001 per night (USD)VRBO
- From $1816 per night (USD)
VRBO
3 Spacious Suites w\/ Living Area & Private Patio! Beachfront Property with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 15
Nestled along the stunning coastline, our newly renovated resort offers a tranquil escape from the everyday hustle and b ...
From $1816 per night (USD)VRBO
- From $494 per night (USD)
VRBO
Best Location! Beachfront Property with Outdoor Pool, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $494 per night (USD)VRBO
- From $447 per night (USD)
VRBO
Fun Under the Sun! Beachfront, w\/ Pool Onsite, Free Parking, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $447 per night (USD)VRBO
- From $487 per night (USD)
VRBO
Dive Into Your Dream Vacation! With Pool, Beachfront Location, Pet-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $487 per night (USD)VRBO
- From $511 per night (USD)
VRBO
Steps Away from the Beach! Enjoy Your Own Patio, Outdoor Pool, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $511 per night (USD)VRBO
- From $599 per night (USD)
VRBO
Summer Escapade! Onsite Pool, Steps from the Beach, Pets Allowed, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $599 per night (USD)VRBO
- From $574 per night (USD)
VRBO
Dream Paradise! Beachfront Property with Pool, Free Parking, Partial Ocean View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $574 per night (USD)VRBO
- From $1028 per night (USD)
VRBO
Best Vacation Choice! Outdoor Pool, Beachfront Location, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1028 per night (USD)VRBO
- From $1331 per night (USD)
VRBO
Enjoy a Hassle-free Stay! Unit w\/ Full Kitchen, Beachfront, Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1331 per night (USD)VRBO
- From $377 per night (USD)
Expedia
Luxurious canal-front home with private heated pool, spa, firepit, patio, & dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Luxurious Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $377 per night (USD)Expedia
- From $238 per night (USD)
VRBO
Charming Islamorada house with waterfront, private dock and beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Islamorada, this delightful house offers a peaceful and serene retreat for guests. With 2 bedrooms, including ...
From $238 per night (USD)VRBO
- From $2935 per night (USD)
VRBO
Keys to Relaxation! Pool, Pets Allowed, Short Drive to Florida Keys Airport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $2935 per night (USD)VRBO
- From $835 per night (USD)
VRBO
Your Islamorada Hideaway! Beachfront Accommodation. Onsite Pool, Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $835 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Coastal Gem! Water Activities Onsite, Pool, Private Patio, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $700 per night (USD)VRBO
- From $1976 per night (USD)
VRBO
High Tides and Good Vibes! 4 Spacious Units, Outdoor Pool, Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1976 per night (USD)VRBO
- From $1035 per night (USD)
VRBO
Coastal Retreat! Pool, Pets Allowed, Minutes to Indian Key Historic State Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1035 per night (USD)VRBO
- From $1482 per night (USD)
VRBO
Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1482 per night (USD)VRBO
- From $1020 per night (USD)
VRBO
Beach Bliss, Just Steps to the Ocean! Outdoor Pool, Near Coral Bay Marina
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1020 per night (USD)VRBO
- From $1331 per night (USD)
VRBO
Dip Your Toes In The Sand! Beachfront, Pool, Near History of Diving Museum
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $1331 per night (USD)VRBO
- From $511 per night (USD)
VRBO
Come Create Memories w\/ Fun-filled Adventures at this Paradise! Beachfront, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. O ...
From $511 per night (USD)VRBO