Islamorada Rentals
From $192 per night (USD)VRBO
Beautiful water front home, private dock in Islamorada, World Fishing Capital
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
This two-story house is located on an ocean access canal that is literally minutes from the Atlantic Ocean. Guest can do ...
From $192 per night (USD)VRBO
From $232 per night (USD)VRBO
Oceanfront condo in Islamorada, amazing sunrise views, renovated in 2019!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Watch the sunrise from your private balconies in both bedrooms overlooking the Atlantic ocean, and walk across the stree ...
From $232 per night (USD)VRBO
From $205 per night (USD)VRBO
Off the beaten path in one of Islamorada’s hidden gem of a community!.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation like a local! This charming 2 bedroom, 2 bath home is located in one of Islamorada’s quaintest and quietest nei ...
From $205 per night (USD)VRBO
From $2880 per night (USD)VRBO
Open Ocean Views - 2 separate properties -House & Cottage With Dockage & Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
We privately own a total of 5 boutique vacation rentals in Islamorada: VRBO listing #1576833 (5 bedroom) VRBO listing #1 ...
From $2880 per night (USD)VRBO
From $263 per night (USD)VRBO
Key West Beachfront Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for the ultimate Florida Keys escape? Come enjoy the best boating in the Upper Keys! New Dock is now COMPLETE! ...
From $263 per night (USD)VRBO
From $739 per night (USD)VRBO
Private Cottage on Bayfront Estate – Pool, Beach, and Boating Paradise
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Garden View Cottage at Mermaid's Bay Boutique Estate, a serene hideaway located in the heart of Islamorad ...
From $739 per night (USD)VRBO
From $433 per night (USD)VRBO
Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This lovely oceanfront home is at Mile Marker 85 in exclusive An ...
From $433 per night (USD)VRBO
From $417 per night (USD)Expedia
New Construction home. 50' Dock w/ Pool & Hot Tub. Just S. of Tavernier Creek
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful Conch style home was completed in 2019. The house is a 2000 sq ft. 3 bedroom 2 bath home, each of it's 3 ...
From $417 per night (USD)Expedia
From $523 per night (USD)VRBO
NEW Luxury Modern Coastal Home in Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This New construction has all the bells and whistles to make your stay unforgettable. Located in the heart of Islamorada ...
From $523 per night (USD)VRBO
From $2408 per night (USD)VRBO
Oceanfront Estate with 4 Cozy Cottages
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave o ...
From $2408 per night (USD)VRBO
From $991 per night (USD)VRBO
Charming cottage on the Florida Bay in the heart of Islamorada with pool, dockage, beach + more
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Bay View Cottage is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Isl ...
From $991 per night (USD)VRBO
From $122 per night (USD)VRBO
Modern one bedroom apartment with beautiful garden view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful, modern updated unit is absolutely beautiful with a private balcony with a wonderful garden view. Homey t ...
From $122 per night (USD)VRBO
From $380 per night (USD)VRBO
5 Star Modern Oceanfront Islamorada Townhome on the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Tw ...
From $380 per night (USD)VRBO
From $211 per night (USD)Expedia
Relaxing waterfront retreat with boat dock & amazing ocean views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Paradise Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $211 per night (USD)Expedia
From $433 per night (USD)VRBO
Oceanside Getaway: Renovated Home with Boat Slip, Pool & Beach - Gated community
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Palm La Mar, a luxury vacation rental located in the exclusive oceanfront gated community of Anglers Reef in Islamorada, ...
From $433 per night (USD)VRBO
From $204 per night (USD)Expedia
Florida Keys Chic
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy breathtaking sunsets from your very own private beach in this Florida Keys Chic townhome!!! Beautiful 3 bedroom 2 ...
From $204 per night (USD)Expedia
From $829 per night (USD)VRBO
Paradise Awaits!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful canal front Tavernier, FL home with minutes to the bay and easy ocean access through Tavernier Creek. Newly re ...
From $829 per night (USD)VRBO
From $432 per night (USD)Expedia
Waterfront Home in Islamorada with outdoor kitchen, pool, spa, boat dockage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Tut’s Cay located in Islamorada in the Florida Keys. Our home is centrally located in our favorite part of th ...
From $432 per night (USD)Expedia
From $445 per night (USD)VRBO
Mini Ray's of Sunshine
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Mini Ray's of Sunshine - Beautiful New Pool Home located in a gated community in the Heart of Islamorada. This home, des ...
From $445 per night (USD)VRBO
From $845 per night (USD)Expedia
Hidden Gem Duplex in Heart of Islamorada! Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This truly is a Hidden Gem in the heart of Islamorada. Nestled in the trees just a few steps from one of the mo ...
From $845 per night (USD)Expedia
From $160 per night (USD)VRBO
Beautiful 1 bedroom apartment with stunning open water view Apt 317
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Premier 1 bedroom unit with both that stunning direct open water bay view and a view of the pool off the balcony. Beauti ...
From $160 per night (USD)VRBO
From $1432 per night (USD)VRBO
Blue Dolphin Oceanfront Estate, Millionaire's Row, Private Saltwater Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding ...
From $1432 per night (USD)VRBO
From $881 per night (USD)VRBO
Venetian Shores Islamorada New Home w/dock & pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Located in Venetian Shores, Islamorada Luxurious bayside waterfront home on a wide canal with easy access to the ocean ...
From $881 per night (USD)VRBO
From $354 per night (USD)VRBO
A 57-foot trawler in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in a friendly marina with a restaurants, gift shop, tiki bar, kayaks, jet skis, and charter fishing boats minute ...
From $354 per night (USD)VRBO
From $474 per night (USD)VRBO
Boat, Fish, Swim from Your Own 70' Dock!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come Play! Your 70-foot private dock provides instant access to fun – whether boating, fishing, swimming or relaxing und ...
From $474 per night (USD)VRBO
From $403 per night (USD)VRBO
Sea Glass Cottage Beautiful Canal Front Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sea Glass Cottage 2b 2b canal front home. Bring your boat or two, and enjoy your vacation or holiday relaxing and playi ...
From $403 per night (USD)VRBO
From $203 per night (USD)VRBO
Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a quaint, ocean side condo with full amenities and easy access for fishing, diving, snorkeling and much more.The ...
From $203 per night (USD)VRBO
From $640 per night (USD)VRBO
The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital o ...
From $640 per night (USD)VRBO
From $1018 per night (USD)VRBO
Private Beachfront Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Village of Islamorada - Vacation Rental License No. 24-0248 This home is remodeled every year in some way or form...We ...
From $1018 per night (USD)VRBO
From $216 per night (USD)VRBO
October last Minute Special ...Bayside Condo with Beach, Pool, Marina & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
October Special 10/18 to 11/2 Your escape to our tropical paradise begins as you enter through the private gates of our ...
From $216 per night (USD)VRBO
From $1463 per night (USD)VRBO
Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
OSPREY BAY VILLA – Your private bayfront escape in the heart of Islamorada, Florida Keys! Relax and enjoy incredible p ...
From $1463 per night (USD)VRBO
From $413 per night (USD)Expedia
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
"Windley Cottage" is a private home in the exclusive gated community of Angler's Reef in Islamorada. This welcoming, ...
From $413 per night (USD)Expedia
From $239 per night (USD)VRBO
Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Discounted 3 to 6 months rentals. Plan your perfect getaways to paradise. 1/1 Fully Renovated Beautifully Designed Condo ...
From $239 per night (USD)VRBO
From $630 per night (USD)VRBO
GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Contact owner for rates and availability at (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital ...
From $630 per night (USD)VRBO
From $830 per night (USD)VRBO
Beach Dream House, relax and enjoy the clear waters of Islamorada FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun risi ...
From $830 per night (USD)VRBO
From $432 per night (USD)VRBO
10% discount on last minute SUMMER RATES in Paradise at Angler's Reef ! ENJOY
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our house is located in Islamorada, FL, the fishing capital of the world. Our single-family, Key-style home is located i ...
From $432 per night (USD)VRBO
From $152 per night (USD)VRBO
NEW-Summer Sea - Sweet updated 1B Apartment w/ Garden View Apt 125
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 bedroom apartment new to the rental market! Modern and updated, this first floor unit has a gorgeous kitchen with stai ...
From $152 per night (USD)VRBO
From $445 per night (USD)VRBO
Stunning Bayfront Townhouse with Boat Slip/ Marina Access - A Luxurious Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Our Cozy Townhouse at Futura Yacht Club! Nestled right by the ocean, our townhouse offers a peaceful escape ...
From $445 per night (USD)VRBO
From $2676 per night (USD)VRBO
Caribee Beach House ~ Private Islamorada Beach Estate W/ Heated Pool & Dockage
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Caribee Beach House! Discover the enchanting charm of Caribee Beach House, where the timeless allure of old- ...
From $2676 per night (USD)VRBO
From $330 per night (USD)VRBO
Anglers Reef Islamorada Vacation Rental 2/2.5 updated 131 Anglers Way
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Village of Islamorada license #24-0369 131 Anglers Way, Islamorada, FL This Villa has 2 bedrooms (one with king bed and ...
From $330 per night (USD)VRBO
From $630 per night (USD)VRBO
GREAT LOCATION !!! White Marlin Beach House, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Contact owner for rates and availability (305-431-2006). Relax in Islamorada, Florida Keys... 'Sport Fishing Capital of ...
From $630 per night (USD)VRBO
From $696 per night (USD)VRBO
Harbor Hideaway ~ Island style beach house with pool, dockage & bay views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Harbor Hideaway! Escape to Harbor Hideaway, your perfect tropical retreat situated on the tranquil shores of ...
From $696 per night (USD)VRBO
From $388 per night (USD)VRBO
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
***June 2022 - Installed a new AC with Germicidal UV light air purifier, which improves air quality by sterilizing mol ...
From $388 per night (USD)VRBO
From $270 per night (USD)VRBO
Spacious Home in Islamorada with boat dock, private beach, & Fast
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
**Please contact owner directly via email if dates do not appear on calendar** There is also an in-laws quarter 1/1 avai ...
From $270 per night (USD)VRBO
From $1033 per night (USD)VRBO
New home with 95' of dock, pool with breathtaking Atlantic Ocean Views.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
New 4br/3bth home off Tavernier Creek, Ocean side with 95' of dock and lowered dock area for boarding kayaks and paddle ...
From $1033 per night (USD)VRBO
From $1406 per night (USD)VRBO
Islamorada Oceanfront Estate, Pool, Beach Cottages-- Sea Ranch -- Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Island Villa Rental Properties offers this two adorable, private cottages right on the Atlantic Ocean. Located in the he ...
From $1406 per night (USD)VRBO
From $803 per night (USD)VRBO
Beautiful 7 BR estate in Islamorada, FL keys, with pool, dockage, & sandy beach!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
Island Villa Rental Properties offers fantastic panoramic views of the Atlantic Ocean from this 7 BR, oceanfront home in ...
From $803 per night (USD)VRBO
From $318 per night (USD)Expedia
Ocean View with protected dock on lagoon with private boat ramp
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Large 3/2 with ground level carport. Lagoon side screened porch 50' x 10'. Terrace on Ocean side is open. Boat acces ...
From $318 per night (USD)Expedia
From $230 per night (USD)VRBO
Escape to Paradise in Islamorada!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 11
Welcome to your perfect family-friendly getaway in the heart of Islamorada, Florida! Nestled between the sun-soaked shor ...
From $230 per night (USD)VRBO
From $592 per night (USD)Expedia
ISLAMORADA BEACH HOUSE
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Luxury Waterfront Home in Exclusive Port Antigua – Islamorada, FL Escape to this stunning 4,200 sq. ft. waterfront retr ...
From $592 per night (USD)Expedia
From $576 per night (USD)VRBO
Impressive Resort Like 5 Bedroom / 4.5 Baths with Pool & Dockage in Islamorada!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Located on a cul-de-sac in the charming city of Islamorada, this beautifully- appointed five-bedroom, four and a half-ba ...
From $576 per night (USD)VRBO
From $234 per night (USD)Expedia
Spacious 3 bedroom home in Plantation key with 30 foot dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Make wonderful memories at this unique and family-friendly waterfront townhouse located on a deep-water canal with 30 fo ...
From $234 per night (USD)Expedia
From $866 per night (USD)VRBO
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Angler's Reef is located at MM85 in Islamorada, the heart of the Florida Keys. Our gated community is made up of 52 luxu ...
From $866 per night (USD)VRBO
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On the water in Islamorada elevated detached unit!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Topsider resort is a unique water front property where all the units are elevated and detached featuring 2 bedrooms & 2 ...
Click For PricingExpedia
From $551 per night (USD)VRBO
Islamorada retreat \"Bungalow Blue\" w/ heated pool, Bikes, BBQ, amenities galore!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to paradise! Completely remodeled and immaculately maintained... Bungalow Blue is nestled away in the quiet qua ...
From $551 per night (USD)VRBO
Click For PricingExpedia
Beautiful estate nestled in a secluded cove on the ocean, 60 ft dock, guesthouse
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Meticulously maintained estate on the water with 60ft doc space and a lift. Incredible sunrises and sunsets from 3rd st ...
Click For PricingExpedia
From $348 per night (USD)VRBO
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 $348 per night (USD)VRBO
From $402 per night (USD)Expedia
Modern Cozy Beachouse Gem
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Elegant modern coastal gem! With beautiful canal views as well as incredible views of native area. Quiet, peaceful home ...
From $402 per night (USD)Expedia
From $293 per night (USD)VRBO
Large Keys Home in Heart of Tavernier with 50 ft of deep water dock.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 11
Incredibly comfortable home located in the heart of Tavernier Key Mile Marker 90. Large home featuring incorporated do ...
From $293 per night (USD)VRBO
From $120 per night (USD)Expedia
Charming oceanfront condo with pool, beach access, tennis, & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Escape to the Keys A6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $120 per night (USD)Expedia
From $588 per night (USD)VRBO
🌴 Oceanview Islamorada Penthouse 3BR 2 BA Sunrise Views, Pool & Weekly Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
🌴 Welcome to Your Islamorada Escape 🌴 Keys Oceanview Penthouse – Weekly Rental in Islamorada Stay in one of the only ...
From $588 per night (USD)VRBO
From $173 per night (USD)VRBO
Home in Paradise- Tavernier Cottage,p Pool & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Totally remodeled, canal front home, quiet and in the nicest neighborhoods (Plantation Key Colony). Situated on the bays ...
From $173 per night (USD)VRBO
From $976 per night (USD)VRBO
Oceanfront 4-BR w/ private 31' Boat Slip Included, Pool & Beach, gourmet kitchen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your private Islamorada oasis — an oceanfront 4-bed, 3-bath home with a newly renovated gourmet kitchen, brig ...
From $976 per night (USD)VRBO
From $568 per night (USD)VRBO
Open February 2024! \"Paradise South\" ~ Chic Island Home with Pool & Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Paradise South! This delightful 3 bedroom, 2 bath home in the heart of Plantation Key welcomes you for your ...
From $568 per night (USD)VRBO
Click For PricingVRBO
Tropical Vacation Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Quiet neighborhood located on a canal one block from the Atlantic Ocean. Home built in 2019, 2900 SF. Close to restauran ...
Click For PricingVRBO
From $626 per night (USD)VRBO
Island Time - Plantation Key Home with 4 beds & 3 baths with Pool & Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Island Time! This newly constructed canal front residence located in the heart of Plantation Key is sure to ...
From $626 per night (USD)VRBO
From $352 per night (USD)VRBO
Beautiful, Spacious, Single Story Home - Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This single-story canal front home located in the heart of Islamorada (MM86) in the Florida Keys-fishing capital of the ...
From $352 per night (USD)VRBO
From $277 per night (USD)VRBO
TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
New In Ground Heated pool , Just remodeled with new furniture, flat screen tvs throughout ( including the patio) and a d ...
From $277 per night (USD)VRBO
From $429 per night (USD)VRBO
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, w ...
From $429 per night (USD)VRBO
From $731 per night (USD)Expedia
Coconut Palm South,1 King Bed, 2 Full Beds, 1 Pull Out
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
1 King Bed, 2 Full Beds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, tea ...
From $731 per night (USD)Expedia
From $529 per night (USD)VRBO
Fish Tail Palm Ocean View 1 Queen Bed, and 1 Pull Out
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ocean View 1 Queen Bed, and 1 Pull Out. Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, ...
From $529 per night (USD)VRBO
From $1622 per night (USD)Expedia
Royal Palm South 3 Bedrooms, 3 Baths, Ocean Front, Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
King, Queen2 twins, 1 pullout. Boat Dockage Custom designed and built from the ground up by resort owner Phil Sena wit ...
From $1622 per night (USD)Expedia
From $633 per night (USD)VRBO
Malayan Palm North 2 Bedrooms, 1 Bath, Garden View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Poolside,2 Queen Beds,1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks ...
From $633 per night (USD)VRBO
From $189 per night (USD)VRBO
Spectacular Penthouse w/Panoramic Open Water Views-New rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Fantastic Penthouse Apartment is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacul ...
From $189 per night (USD)VRBO
From $199 per night (USD)VRBO
Eclectic Easeful Stay At The Keys!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy this spacious, airy, and recently renovated condo at Summer Sea in beautiful Tavernier, Florida. The buil ...
From $199 per night (USD)VRBO
From $321 per night (USD)Expedia
Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to island time at beautiful Anglers Reef, the perfect way to experience and relax in the Florida Keys. Our hom ...
From $321 per night (USD)Expedia
From $295 per night (USD)VRBO
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $295 per night (USD)VRBO
From $294 per night (USD)VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $294 per night (USD)VRBO
From $296 per night (USD)VRBO
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $296 per night (USD)VRBO
From $291 per night (USD)VRBO
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $291 per night (USD)VRBO
From $295 per night (USD)VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $295 per night (USD)VRBO
From $296 per night (USD)VRBO
Just What You Were Looking For! Free Breakfast, Onsite Pool, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $296 per night (USD)VRBO
From $736 per night (USD)VRBO
4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4-bedroom, 3.5 bath home in Angler's Reef. Located at MM85, this tastefully decorated, open floor plan feature ...
From $736 per night (USD)VRBO
From $411 per night (USD)VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $411 per night (USD)VRBO
From $411 per night (USD)VRBO
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $411 per night (USD)VRBO
From $411 per night (USD)VRBO
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $411 per night (USD)VRBO
From $266 per night (USD)VRBO
Canal-Front Florida Keys Home w/ Dock!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Ocean breezes and beautiful water views are in store at this 2-bedroom, 2-bathroom home. This Florida Keys vacation rent ...
From $266 per night (USD)VRBO
From $329 per night (USD)VRBO
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $329 per night (USD)VRBO
From $329 per night (USD)VRBO
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $329 per night (USD)VRBO
From $297 per night (USD)VRBO
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $297 per night (USD)VRBO
From $297 per night (USD)VRBO
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $297 per night (USD)VRBO
From $297 per night (USD)VRBO
Ideal Location! Onsite Pool, Free Breakfast, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beachfront home offers a picture-perfect vantage point to see the famous Florida Keys sunset. We are conveniently si ...
From $297 per night (USD)VRBO
From $231 per night (USD)VRBO
Trendy canal-front home with dock, full kitchen, central AC, & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Salt House Swank Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $231 per night (USD)VRBO
Click For PricingExpedia
Pristine canal-front home with heated pool and access to open water
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Beautifully appointed getaway perfectly situated to allow exploration of the mangroves or the open water, since Tavernie ...
Click For PricingExpedia
Click For PricingVRBO
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 PricingVRBO
From $697 per night (USD)VRBO
Luxury Home with 60' Deep Water Dock, Waterfall Pool, HotTub, A/C and WiFi
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Minimum 28 day stay. Dreaming of a FL Keys vacation where you can boat, fish, dive, snorkel or stay home and swim in yo ...
From $697 per night (USD)VRBO
From $775 per night (USD)VRBO
Islamorada paradise vacation home in sought after Venation shores
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location! Venetian Shores is the premier luxury private community with deep water access to Snake creek, which ...
From $775 per night (USD)VRBO
From $335 per night (USD)VRBO
Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $335 per night (USD)VRBO
From $356 per night (USD)VRBO
Premium Units w/ Ocean Views & Balcony! Marina, Pets Allowed, Beach Access!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $356 per night (USD)VRBO
From $263 per night (USD)VRBO
Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each furnished room features premium bedding and free Wi-Fi access. Our pet-friendly private beach resort has its boat r ...
From $263 per night (USD)VRBO