Islamorada Rentals
From $540 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 $540 per night (USD)VRBO
From $430 per night (USD)VRBO
Spacious Islamorada Canal-Front Home w\/ Dock\/ 5 Bedroom\/ 4 Baths
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious home with open area for dining/entertaining and view of canal. Master bedroom/bath on upper level with extra si ...
From $430 per night (USD)VRBO
From $173 per night (USD)VRBO
Home in Paradise- Islamorada Cottage,p Pool & Dockage
- Bedrooms:
- 3
- 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 $1125 per night (USD)Expedia
Jamaican Palm House 3 Bedrooms, 2 Bath, Poolside
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Poolside,3 Queen Beds,1 Pull Out Welcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. E ...
From $1125 per night (USD)Expedia
From $663 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 $663 per night (USD)VRBO
From $404 per night (USD)VRBO
TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE\/VIEW COMPLETELY REMODELED
- Bedrooms:
- 3
- 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 $404 per night (USD)VRBO
From $731 per night (USD)VRBO
Canary Island Palm South 2 Bedrooms, 2 Baths, Poolside
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Poolside,1 King Bed, 2 Queen Beds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahog ...
From $731 per night (USD)VRBO
From $630 per night (USD)Expedia
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 $630 per night (USD)Expedia
From $675 per night (USD)VRBO
Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoga ...
From $675 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 $900 per night (USD)VRBO
Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Partial Ocean View 1 King Bed, 1 Queen Bed, 1 Pull Out Resort guests stay in warm and inviting Caribbean-style homes. R ...
From $900 per night (USD)VRBO
From $399 per night (USD)VRBO
Beautiful Venetian Shores canal home with dockage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
130 Stromboli Drive - Beautiful Venetian Shores canal home that has two-bedroom two bath upstairs and a one-bedroom one ...
From $399 per night (USD)VRBO
From $422 per night (USD)VRBO
D Casas Morada*Heated Pool*Dockage*Boat Lift
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
D Casa Morada is newly remodeled and located withing walking distance to Robbie's of Islamorada and just a half a mile t ...
From $422 per night (USD)VRBO
From $622 per night (USD)VRBO
Impressive Resort Like 5 Bedroom \/ 4.5 Baths with Pool & Dockage in Islamorada!
- Bedrooms:
- 5
- 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 $622 per night (USD)VRBO
From $908 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 $908 per night (USD)VRBO
From $261 per night (USD)VRBO
Blue Haven ~ Modern Downtown Islamorada Home with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Blue Haven! This immaculate 3 bedroom / 2.5 bathroom home provides the perfect home base for your next Flor ...
From $261 per night (USD)VRBO
From $184 per night (USD)VRBO
DECEMBER SPECIAL!!! 800.00 for any week stay in December 2024
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Your escape to our tropical paradise begins as you enter through the private gates of our community at Futura Yacht Club ...
From $184 per night (USD)VRBO
From $522 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 $522 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:
- 2
- 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 $571 per night (USD)VRBO
ULTIMATE outdoor living area at this 4\/4 canal home with pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This beautifully remodeled home in desirable Plantation Key Colony has the sought-after amenities of a large resort, in ...
From $571 per night (USD)VRBO
From $182 per night (USD)VRBO
3 bed \/ 2 bath in the heart of Tavernier
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to the Cottage on Pearl! Escape the ordinary office routine and enjoy the freedom of working from our home! Wit ...
From $182 per night (USD)VRBO
From $451 per night (USD)VRBO
Keys Waterfront House with large pool 30' Dock w\/ 50 Amp power 10% off Nov-Feb
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
NOW OFFERING A SPECIAL RATE OF 10% OFF FOR BOOKINGS FROM DECEMBER 2024 THROUGH FEBUARY 2025 ONLY, Fishermans parad ...
From $451 per night (USD)VRBO
From $1122 per night (USD)VRBO
Tropical retreat where location meets quintessential Keys vacation home.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Heart of Morada - This unique townhome is located bay front at Mile Marker 81.5 on U.S. Highway 1 in the heart of downto ...
From $1122 per night (USD)VRBO
From $262 per night (USD)Expedia
Best Location for Your best vacation!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Best Home to Share with Family and Friends! This Beautiful Home consists of 2 levels with 2 separate units. The 1st leve ...
From $262 per night (USD)Expedia
From $492 per night (USD)VRBO
New saltwater pool, pet friendly, waterfront house with dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,0 ...
From $492 per night (USD)VRBO
From $578 per night (USD)VRBO
NEW Luxury Modern Coastal Home in Islamorada
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This New construction has all the bells and whistles to make your stay unforgettable. Located in the heart of Islamorada ...
From $578 per night (USD)VRBO
From $437 per night (USD)VRBO
Beautiful New Pool Home located in a gated community in the Heart of Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
29 Flamingo Hammock Road - This Beautiful Ground-Level Vacation Retreat awaits your arrival. Walk into this home and you ...
From $437 per night (USD)VRBO
From $262 per night (USD)VRBO
Fantastic Home in the Fishing Capital of the World!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This is a custom-built Mediterranean style home located in an exclusive community with a private beach for owners and re ...
From $262 per night (USD)VRBO
From $441 per night (USD)VRBO
Spacious & Beautifully remodeled condo w\/ sunset views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
LIVE and LOVE THE FLORIDA KEYS LIFE! Gorgeous completely remodeled spacious condo in the highly sought after Futura Yach ...
From $441 per night (USD)VRBO
From $421 per night (USD)VRBO
Futura Yacht Club Bayfront Townhome with Endless Sunsets!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Endless Sunsets!! This is a beautiful Bayfront Townhome in Islamorada's popular Futura Yacht Club. 3 level townhome w ...
From $421 per night (USD)VRBO
From $517 per night (USD)VRBO
Venetian Shores Home -DOCK remodeled 3\/3 POOL\/Hot Tub! Deep water Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
126 Palermo Drive Check out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, ...
From $517 per night (USD)VRBO
From $1559 per night (USD)VRBO
Large bay-front home with dockage, pool and beach in the heart of Islamorada
- Bedrooms:
- 8
- Bathrooms:
- 4
- Sleeps:
- 10
The Dock View House is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Isla ...
From $1559 per night (USD)VRBO
From $146 per night (USD)VRBO
Great location in Islamorada, FL.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Great location in the heart of paradise! Small building in Islamorada, FL - centrally located. Next to great restauran ...
From $146 per night (USD)VRBO
From $347 per night (USD)VRBO
Home in Islamorada Florida
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Water Front modern home perfectly situated on the Bay side. Located on a deep-water canal that offers all sorts of enjoy ...
From $347 per night (USD)VRBO
From $300 per night (USD)VRBO
Waterfront Pool Home with great dockage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Adorable waterfront pool home in Tavernier! Great dockage close to Tavernier Creek for easy bay and ocean access. Cozy c ...
From $300 per night (USD)VRBO
From $3005 per night (USD)VRBO
4 BR Ocean front Condo in Islamorada, FL Keys steps away from pool & sandy beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Maison Residences offers world-class oceanfront residences in the Florida Keys. Unit 102 at Maison Residences is a luxur ...
From $3005 per night (USD)VRBO
From $2126 per night (USD)VRBO
Ocean Front 4 Bedroom Estate with Private Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features ...
From $2126 per night (USD)VRBO
From $2066 per night (USD)VRBO
5 Bedroom Ocean Front Pool Home
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Step out the door to your private oceanfront beach with pool and dock at Midnight Runner. The property features two livi ...
From $2066 per night (USD)VRBO
From $199 per night (USD)VRBO
Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of I ...
From $199 per night (USD)VRBO
From $772 per night (USD)VRBO
Islamorada's Premier Waterfront Neighborhood- Venetian Shores!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Casa De Bliss - Canal front Venetian Shores...Unwind on your trip to the Keys at Casa De Bliss. This four bedrooms, four ...
From $772 per night (USD)VRBO
From $470 per night (USD)VRBO
Key Lime Cottage in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Your slice of Islamorada awaits at the Key Lime Cottage! Located in the heart of the Florida Keys yet set in its own oas ...
From $470 per night (USD)VRBO
From $558 per night (USD)VRBO
Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover Your Slice of Islamorada Paradise! Contact Us Directly for Availability Welcome to our newly remodeled, canal ...
From $558 per night (USD)VRBO
From $361 per night (USD)VRBO
Ocean front paradise, 6th story balcony ocean view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Islamorada is the fishing capital of the world, and home to the famous Islamorada sandbar. 🏖️ This condo is a 6th floor ...
From $361 per night (USD)VRBO
From $180 per night (USD)VRBO
Maseri's Hideaway - Beautiful Newly Renovated Townhome in Gorgeous Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to paradise! Come and relax in our beautiful newly renovated townhome in Islamorada. The executive Bay club is ...
From $180 per night (USD)VRBO
From $348 per night (USD)VRBO
Beachfront Islamorada Villa with Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect Islamorada getaway awaits. Sandy Pointe Villa provides panoramic water views overlooking the Florida Bay, ...
From $348 per night (USD)VRBO
From $347 per night (USD)VRBO
Bayfront Islamorada Townhome with Dock & Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy all the wonders Sandy Pointe Townhome has to offer. With breathtaking bay views, deep water dockage and a private ...
From $347 per night (USD)VRBO
From $525 per night (USD)VRBO
Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 15
Welcome to Paradise! This fabulous Keys home with Tommy Bahama décor throughout is a Fisherman & Water Enthusiast's Dre ...
From $525 per night (USD)VRBO
From $456 per night (USD)VRBO
Stunning Ocean Harbour Corner Unit - Panoramic ocean views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This opulent condo is located within Ocean Harbour which is one of Islamorada’s most sought after gated communities feat ...
From $456 per night (USD)VRBO
From $257 per night (USD)VRBO
3 BR 2 Bath Islamorada home with Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Vacation in this cozy canal front home in the heart of Islamorada, midpoint between Miami and Key West. Large upstairs ...
From $257 per night (USD)VRBO
From $429 per night (USD)Expedia
Aqua Villa Starfish @ Mangrove Marina Resort on the waterfront
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Starfish houseboat has 1 Queen bed, 2 Twin Beds . Each houseboat has flat-screen TVs with cable and complimentary Wi ...
From $429 per night (USD)Expedia
From $394 per night (USD)VRBO
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay at the Tipsy Turtle in Angler's Reef! This magnificent home with ocean views from all 4 balconies is located ...
From $394 per night (USD)VRBO
From $445 per night (USD)Expedia
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a la ...
From $445 per night (USD)Expedia
From $443 per night (USD)VRBO
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Angler's Retreat is a 2 bedroom, 2.5 bathroom single-family home with picturesque ocean views, privacy, and space. The p ...
From $443 per night (USD)VRBO
From $715 per night (USD)Expedia
Spectacular Ocean Front Home In Beautiful Islamorada!>Dock,Com Pool, & Prv Bch
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
VRL# 24-0132 we are one of Islamorada’s limited number of licensed weekly vacation homes. This magnificent home with d ...
From $715 per night (USD)Expedia
Click For PricingVRBO
WaterFront community in Islamorada w\/ Marina\/Pool\/Tennis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
20% OFF FROM APRIL-JUNE!!! This 3 bed/2 bath features an open and spacious floor plan! Enjoy king beds, great sound sys ...
Click For PricingVRBO
From $394 per night (USD)Expedia
Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Sea Biscuit houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $394 per night (USD)Expedia
From $398 per night (USD)VRBO
Waterfront Sunset View Aqua Villa at Conch Shell @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Conch Shell houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $398 per night (USD)VRBO
From $484 per night (USD)Expedia
Anglers Dream House; Close To It All - Beach, Pool & Kayaks in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Keezy Does It at Anglers Reef in Islamorada! A charming, oceanfront gated community in the heart of Islamora ...
From $484 per night (USD)Expedia
From $374 per night (USD)VRBO
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
- VR#258 - Saturday check in preferred, message for alternate days. 2 bedroom and 2.5 bath at 117 Anglers Way Slip ava ...
From $374 per night (USD)VRBO
From $416 per night (USD)Expedia
Aqua Lodge Houseboat \"Yellow Tail \"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Are you ready to be adventurous , do something unique and fun? Well, it doesn’t get Yellow Tail houseboat, is a 1 bedro ...
From $416 per night (USD)Expedia
From $417 per night (USD)VRBO
Aqua Lodge Houseboat \"Tarpon\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This Aqua Lodge has a master bedroom with a queen-sized bed, equipped with TV and Air Conditioning unit. The cathedral c ...
From $417 per night (USD)VRBO
From $577 per night (USD)Expedia
Bright & Cheery Pool Front Home with Ocean Views at Anglers Reef in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Angler’s Reef Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths w ...
From $577 per night (USD)Expedia
From $591 per night (USD)VRBO
Aqua Lodge Houseboat \"The Grey Lady\"
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This houseboat has 2 Queen beds, 1 Double bed and 1 Twin bed. The houseboat has a flat-screen TV with cable in the livin ...
From $591 per night (USD)VRBO
From $354 per night (USD)Expedia
Aqua Lodge Houseboat \"Sea Turtle\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Aqua Villas at Mangrove Marina Resorts “Sea Turtle” houseboat, located between Key Largo and Islamorada i ...
From $354 per night (USD)Expedia
From $520 per night (USD)VRBO
Aqua Lodge Houseboat \"Calypso\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
It doesn’t get much more unique than the Aqua Villas at Mangrove Marina. Come experience the adventure of living on the ...
From $520 per night (USD)VRBO
From $489 per night (USD)Expedia
Aqua Lodge Houseboat \"Captain's Quarters\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Aqua Villas at Mangrove Marina Resorts “Captain’s Quarters” houseboat, located between Key Largo and Isla ...
From $489 per night (USD)Expedia
From $216 per night (USD)VRBO
Penthouse view - Futura Yacht Club #604
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Condo #604, 3 Bedrooms, 2.0 Baths, (Sleeps 6) Enjoy penthouse views of the fabulous blue waters of the Atlantic and Flo ...
From $216 per night (USD)VRBO
From $2029 per night (USD)Expedia
Ultra Luxurious 4 Bedroom ocean front Rental home in Islamorada, Florida Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Maison Residences Unit 202, Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS — A world-c ...
From $2029 per night (USD)Expedia
From $570 per night (USD)VRBO
Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay at the Salty Pelican in Angler's Reef! This magnificent home with amazing direct ocean views from the master b ...
From $570 per night (USD)VRBO
From $487 per night (USD)Expedia
Houseboat offers a rooftop deck for stunning views of the sunrise and sunset.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
The Manatee houseboat has 1 King bed and 3 Double beds. Each houseboat has flat-screen TVs with cable and complimentary ...
From $487 per night (USD)Expedia
From $607 per night (USD)VRBO
Renovated - Boat slip, pool, beach - Anglers Reef oceanside gated community
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Palm La Mar, a luxury vacation rental located in the exclusive oceanfront gated community of Anglers Reef in Islamorada, ...
From $607 per night (USD)VRBO
From $450 per night (USD)Expedia
Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool
- Bedrooms:
- 3
- 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 $450 per night (USD)Expedia
From $946 per night (USD)VRBO
Waterfront Home in Islamorada with outdoor kitchen, pool, spa, boat dockage
- Bedrooms:
- 6
- 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 $946 per night (USD)VRBO
From $422 per night (USD)Expedia
Islamorada Anglers Reef ~ Stay in paradise for your next Vacation
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 128 Anglers Way: "Morada Daydreaming". Our home away from home in the Angler's Reef exclusive gated community ...
From $422 per night (USD)Expedia
From $500 per night (USD)VRBO
Prestigious Venetian Shores with private Pool and Snake Creek View
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect island get-away in beautiful Islamorada, the Fishing Capital of the World. Desirable Venetian Shores is an e ...
From $500 per night (USD)VRBO
From $515 per night (USD)Expedia
Islamorada Anglers Reef! “Sandbar Bungalow Villa\" AMAZING! Middle row location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
AMAZING MIDDLE ROW! COMPLETELY UPDATED! BOAT SLIP AVAILABLE This oceanfront resort is a boutique complex of 52 homes ins ...
From $515 per night (USD)Expedia
From $450 per night (USD)VRBO
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths ...
From $450 per night (USD)VRBO
From $1958 per night (USD)Expedia
Entire Compound on Gated Bayfront Property
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
PROPERTY NAME: Little Bay Compound 82246 Overseas Highway, Islamorada, Florida LOCATION: Cottage and Two Story Duplex ...
From $1958 per night (USD)Expedia
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Beautiful Waterfront Townhome in Islamorada with Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Cozily furnished bayside townhome & boat slip (option to rent), located in desirable 'Futura Yacht Club' gated community ...
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From $920 per night (USD)Expedia
Keys home overlooking the ocean and beautiful sunrises!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful oceanfront residence with pool, and modern renovations. Located in desirable Islamorada with access to a priva ...
From $920 per night (USD)Expedia
From $851 per night (USD)VRBO
Isla Key Acaí: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $851 per night (USD)VRBO
From $507 per night (USD)Expedia
Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $507 per night (USD)Expedia
From $913 per night (USD)VRBO
Isla Guava: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $913 per night (USD)VRBO
From $319 per night (USD)Expedia
The Finn in the Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Finn houseboat has 1 Queen bed. This houseboat has 2 SMART flat-screen TVs and complimentary Wi-Fi. The kitchen feat ...
From $319 per night (USD)Expedia
From $303 per night (USD)VRBO
Leisure Inn Islamorada - 3\/2 canal home on a double lot, bring all of the toys!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This charming Florida home is situated on a double lot with a full sea basin on an ocean side, deep water canal...second ...
From $303 per night (USD)VRBO
From $450 per night (USD)Expedia
Cosy Cottage in Islamorada with private garden & pool - 6 pers.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Flamingo Cottage! The pretty cottage is located in Islamorada, the heart of the Keys. A part of the interior ...
From $450 per night (USD)Expedia
From $1089 per night (USD)VRBO
Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $1089 per night (USD)VRBO
From $245 per night (USD)Expedia
Gorgeous Beach Bungalow Just Steps from Private Sandy Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You have found a sandy beach paradise in the Florida Keys! Located just 4 houses from a secret, sandy beach, Little Pea ...
From $245 per night (USD)Expedia
From $379 per night (USD)VRBO
Escape to beautiful Islamorada!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Located 90 minutes from Miami and 20 minutes to the world-famous Tiki Bar sandbar (dock to anchor) one of the best in ...
From $379 per night (USD)VRBO
From $4410 per night (USD)Expedia
Wander Islamorada Island
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Wander Islamorada Island is an extraordinary private oasis nestled in the Florida Keys. This gated Caribbean-style retre ...
From $4410 per night (USD)Expedia
From $628 per night (USD)VRBO
Waterfront pool home with 70' of dock for your boat with lift in Islamorada!!!!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Luxury Waterfront Vacation Home in Islamorada Escape to paradise in this stunning waterfront vacation home located in t ...
From $628 per night (USD)VRBO
From $270 per night (USD)Expedia
Charming canal front with Ocean access 2-bedroom house in peaceful Tavernier
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in Tavernier, enjoy what this 2-bedroom, 2 bathrooms house has to offer. This perfect and peaceful retreat featu ...
From $270 per night (USD)Expedia
From $642 per night (USD)VRBO
Ultimate Beach Relaxation: Resort w\/ Marina and Outdoor Pool | Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $642 per night (USD)VRBO
From $710 per night (USD)VRBO
Beachfront Room with Private Access & Breathtaking Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $710 per night (USD)VRBO
From $710 per night (USD)VRBO
Waterfront Retreat Perfect Romantic Couple Getaway | Free Parking and Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $710 per night (USD)VRBO
From $676 per night (USD)VRBO
Island Getaway: Relaxing Room w\/ Balcony Steps to Sandy Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $676 per night (USD)VRBO
From $2555 per night (USD)VRBO
4 Family-friendly Rooms w\/ Balcony | Refreshing Outdoor Pool & Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $2555 per night (USD)VRBO
From $1916 per night (USD)VRBO
Beachside Solace: Room for Your Perfect Vacation | 3 Family Ready Stays
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $1916 per night (USD)VRBO
From $949 per night (USD)VRBO
Beachfront Stay Perfect for Island Couple Retreat | Suite w\/ Balcony
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $949 per night (USD)VRBO
From $2118 per night (USD)VRBO
Family Beach Getaway | 3 Relaxing Rooms w\/ Balcony | Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $2118 per night (USD)VRBO