Islamorada Rentals
From $781 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 $781 per night (USD)VRBO
From $233 per night (USD)Expedia
Bayside Condo with Marina, Boat Slips, Pool, Beach and awesome Sunsets
- 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 $233 per night (USD)Expedia
From $505 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 $505 per night (USD)VRBO
From $286 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 $286 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 $347 per night (USD)Expedia
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)Expedia
From $376 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 $376 per night (USD)VRBO
From $2126 per night (USD)Expedia
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
- 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)Expedia
From $2101 per night (USD)VRBO
Charming Ocean Front Pool Home with dockage & pool
- 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 $2101 per night (USD)VRBO
From $144 per night (USD)Expedia
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 $144 per night (USD)Expedia
From $339 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 $339 per night (USD)VRBO
From $355 per night (USD)Expedia
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 $355 per night (USD)Expedia
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 $753 per night (USD)Expedia
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 $753 per night (USD)Expedia
From $530 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 $530 per night (USD)VRBO
From $334 per night (USD)Expedia
Key Lime Cottage in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Relax, Recharge & Explore – Detached Islamorada Cottage w/ Pool, Paddleboards & Fire Pit ☀️ Welcome to your own private ...
From $334 per night (USD)Expedia
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 $313 per night (USD)Expedia
Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip
- 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 $313 per night (USD)Expedia
From $276 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 $276 per night (USD)VRBO
From $525 per night (USD)Expedia
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)Expedia
From $459 per night (USD)VRBO
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 $459 per night (USD)VRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
From $446 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 $446 per night (USD)VRBO
From $354 per night (USD)Expedia
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 $354 per night (USD)Expedia
From $460 per night (USD)VRBO
Keezy Does It - Charming Islamorada Villa in Gated Anglers Reef – Pool & Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Keezy Does It – Anglers Reef, Islamorada BOAT SLIP AVAILABLE: May 11–18 & May 24 – June 6, 2025 Escape to paradise at K ...
From $460 per night (USD)VRBO
From $354 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 $354 per night (USD)Expedia
From $445 per night (USD)VRBO
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
VRL# 25-0132 we are one of Islamorada’s limited number of licensed weekly vacation homes. This magnificent home with di ...
From $445 per night (USD)VRBO
From $452 per night (USD)Expedia
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 $452 per night (USD)Expedia
From $380 per night (USD)VRBO
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 $380 per night (USD)VRBO
From $380 per night (USD)Expedia
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 $380 per night (USD)Expedia
From $445 per night (USD)VRBO
Bright & Cheery Pool Front Home w\/ Optional Boat Slip at Anglers Reef 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 $445 per night (USD)VRBO
From $506 per night (USD)Expedia
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 $506 per night (USD)Expedia
From $354 per night (USD)VRBO
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)VRBO
From $486 per night (USD)Expedia
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 $486 per night (USD)Expedia
From $441 per night (USD)VRBO
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 $441 per night (USD)VRBO
From $249 per night (USD)Expedia
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 $249 per night (USD)Expedia
From $618 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 $618 per night (USD)VRBO
From $1597 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 $1597 per night (USD)Expedia
From $410 per night (USD)VRBO
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
- VR#258 - Saturday check-in. 2 bedroom and 2.5 bath at 117 Anglers Way. Awesome family get-a-away in beautiful Islamor ...
From $410 per night (USD)VRBO
From $403 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 $403 per night (USD)Expedia
From $527 per night (USD)VRBO
Oceanside Getaway: Renovated Home with Boat Slip, Pool & Beach - 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 $527 per night (USD)VRBO
From $471 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 $471 per night (USD)Expedia
From $563 per night (USD)VRBO
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 $563 per night (USD)VRBO
From $389 per night (USD)Expedia
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 $389 per night (USD)Expedia
From $442 per night (USD)VRBO
Warm, sunny, perfect vacation in Islamorada's Anglers Reef
- 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 $442 per night (USD)VRBO
From $517 per night (USD)Expedia
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 $517 per night (USD)Expedia
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $1968 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 $1968 per night (USD)Expedia
From $856 per night (USD)VRBO
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 $856 per night (USD)VRBO
From $488 per night (USD)Expedia
Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $488 per night (USD)Expedia
From $472 per night (USD)VRBO
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $472 per night (USD)VRBO
From $479 per night (USD)Expedia
Isla Key Acaí: Waterfront Boutique Resort, FREE Boat Dockage Sep-Oct Only!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $479 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 $460 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 $460 per night (USD)Expedia
From $571 per night (USD)VRBO
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Community amenities: heated pool, boat dock, BBQ 📍Walk to shops, grocery store, parks, restaurant ...
From $571 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 $238 per night (USD)VRBO
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 $238 per night (USD)VRBO
From $379 per night (USD)Expedia
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)Expedia
From $284 per night (USD)VRBO
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 $284 per night (USD)VRBO
From $628 per night (USD)Expedia
Canal front pool home in Florida key's Islamorada! Access to ocean w\/boat lift!!
- 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)Expedia
From $429 per night (USD)VRBO
Islamorada Anglers Reef Oceanview 2BR Home: Private Beach, Heated Pool, Marina!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
***NEW OWNER SPECIAL*** Welcome to REELaxation! Everything you need for your vacation is here, gorgeous private beach, ...
From $429 per night (USD)VRBO
From $404 per night (USD)Expedia
3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Nestled at the quiet west end of Islamorada, minutes from the Channel 2 and Channel 5 bridges famed for Tarpon fishing, ...
From $404 per night (USD)Expedia
From $266 per night (USD)VRBO
Newer Home in Beautiful Oceanside Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to a unique and serene retreat at a beautiful resort perched on the edge of the Atlantic Ocean. This resort-view ...
From $266 per night (USD)VRBO
From $218 per night (USD)Expedia
3-bedroom House in tranquil Islamorada with Modern Amenities
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 3-bedroom Islamorada retreat. This charming house features 2 queen beds and 2 full beds, p ...
From $218 per night (USD)Expedia
From $511 per night (USD)VRBO
At The Sandbar: Oceanfront, Htd Pool, Free Dockage, GameRoom, EV Charger
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Short Description 🏡 Amenities: Free boat dockage, htd pool, BBQ grill, EV charger 🏓 Game room 📍 Mins to the famous ...
From $511 per night (USD)VRBO
From $286 per night (USD)Expedia
Brand New Ocean Front, Resort Location w\/ Boatslip!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This brand new home and private boat slip is sitting quietly behind a controlled access gate with a personal view of the ...
From $286 per night (USD)Expedia
From $361 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 $361 per night (USD)VRBO
From $417 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 $417 per night (USD)VRBO
From $416 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 $416 per night (USD)VRBO
From $388 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 $388 per night (USD)VRBO
From $1554 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 $1554 per night (USD)VRBO
From $1165 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 $1165 per night (USD)VRBO
From $575 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 $575 per night (USD)VRBO
From $1335 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 $1335 per night (USD)VRBO
From $522 per night (USD)VRBO
Beachfront Retreat in the Heart of Islamorado | Spacious Room w\/ Balcony
- 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 $522 per night (USD)VRBO
From $1781 per night (USD)VRBO
4 Scenic Marina View 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 $1781 per night (USD)VRBO
From $776 per night (USD)VRBO
Beach Getaway: Room with Access to Pristine Sands | 2 Relaxing Rooms
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $776 per night (USD)VRBO
From $891 per night (USD)VRBO
Breathtaking Marina View Room w\/ Balcony | 2 Family Ready Rooms w\/ Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Islamorada's charms: explore the nearby Indian Key Historic Park and don't miss the stunning Theater of the Sea ...
From $891 per night (USD)VRBO
From $445 per night (USD)VRBO
Marina Room with Direct Beach Access | Islamorado Ultimate Retreat
- 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 $445 per night (USD)VRBO
From $586 per night (USD)Expedia
Relax & Unwind at Peaceful Palms – A Luxury Islamorada Escape
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Peaceful Palms, a 3-bedroom, 3-bathroom townhome that’s all about easy, laid-back island living. Tucked away ...
From $586 per night (USD)Expedia
From $1032 per night (USD)VRBO
Bayfront Home with Pool in Islamorada
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 9
This home includes 5 bedrooms, 4.5 baths, elevator, spacious living room and kitchen. Guests can enjoy the open water a ...
From $1032 per night (USD)VRBO
From $585 per night (USD)Expedia
Islamorada's Newest Luxury Address
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Vacation Rental License #25-0283 Welcome to Peaceful Palms, your little slice of paradise in the heart of Islamorada! S ...
From $585 per night (USD)Expedia
From $773 per night (USD)VRBO
Blue Palm Oasis ~ 4 Bedroom Plantation Key Home w\/ Pool & 170` of Dockage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Blue Palm Oasis! Escape to paradise at Blue Palm Oasis, a charming 4-bedroom, 3-bath home located on Plantat ...
From $773 per night (USD)VRBO
From $257 per night (USD)Expedia
Waterfront Florida Keys Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect slice of Old Florida paradise! Tucked away on a spacious waterfront lot, this classic Keys cotta ...
From $257 per night (USD)Expedia
From $609 per night (USD)VRBO
Peaceful Palms Unit 2 – Waterfront Views, Dockage, Pool & Game Room Fun!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful Palms 2 is a brand-new 3-bedroom, 3-bathroom townhome in Islamorada—bright, breezy, and designed for easygoing ...
From $609 per night (USD)VRBO
From $875 per night (USD)Expedia
Oceanfront Oasis in Angler’s Reef with Private Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Escape to this laid-back, oceanfront townhouse in Angler’s Reef, where coastal vibes and easy living come together in th ...
From $875 per night (USD)Expedia
From $1449 per night (USD)VRBO
Luxury Oceanfront Oasis With Deep Water Dockage!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Experience the ultimate coastal getaway at this spectacular 5 bedroom, 5.5 bathroom oceanfront home, complete with deep ...
From $1449 per night (USD)VRBO
From $3026 per night (USD)Expedia
A Premier Oceanfront Estate in Islamorada
- Bedrooms:
- 9
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Ocean’s Edge, a premier oceanfront estate in Islamorada. Nestled along the pristine shores of the Atlantic Oc ...
From $3026 per night (USD)Expedia
From $437 per night (USD)VRBO
Port Antigua Home in a Private Beach & Golf Cart Community
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
Our relaxing 3 STORY, 4 bedroom, 3.5 bathroom home is located in Islamorada, Florida within the Private Beach community ...
From $437 per night (USD)VRBO
From $447 per night (USD)Expedia
Oceanside Resort... Oceanview unit with kayaks, paddleboards and walk in beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Artist's Cottage at Anglers Reef #136 - This beautiful home is located in Angler's Reef, a gated oceanfront communit ...
From $447 per night (USD)Expedia
From $258 per night (USD)VRBO
Relax in this gorgeous townhome while overlooking the sparkling Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Windy Cove #2 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo feat ...
From $258 per night (USD)VRBO
From $407 per night (USD)Expedia
\"Islamorada Waterside Getaway: Prime Fishing, Sunset Views, Beachside Bliss!\"
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Discover the Keys from a unique perspective at this Islamorada rental home, a true haven for fishing enthusiasts! Positi ...
From $407 per night (USD)Expedia
From $562 per night (USD)VRBO
Your Dream Getaway at Anglers Reef
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Anglers Reef Villa Resort 2 Bedroom and 2.5 Bath Villa, in Anglers Reef . An upscale gated community with resort living ...
From $562 per night (USD)VRBO
From $263 per night (USD)Expedia
Key West Beachfront Retreat!
- Bedrooms:
- 3
- 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)Expedia
From $278 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 $278 per night (USD)VRBO
From $482 per night (USD)Expedia
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
***June 2022 - Installed a new AC with Germicidal UV light air purifier, which improves air quality by sterilizing mol ...
From $482 per night (USD)Expedia
From $452 per night (USD)VRBO
Off season special price May, Oct, Nov - Paradise at Angler's Reef ! Enjoy it!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Our house is located in Islamorada, FL, the fishing capital of the world. Our single-family, Key-style home is located i ...
From $452 per night (USD)VRBO
From $405 per night (USD)Expedia
Anglers Reef Islamorada Vacation Rental 2\/2.5 updated 131 Anglers Way
- Bedrooms:
- 3
- 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 $405 per night (USD)Expedia
From $377 per night (USD)VRBO
OCEANFRONT ANGLERS REEF ISLAMORADA HOME-Pool, Dock, Beach, Kayaks, Paddle Boards
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
"Windley Cottage" is a private home in the exclusive gated community of Angler's Reef in Islamorada. This welcoming, ...
From $377 per night (USD)VRBO
From $710 per night (USD)Expedia
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 $710 per night (USD)Expedia