Windley Key Holiday Rentals

Compare Villas, Resorts, & Rentals in Windley Key, Florida, USA

Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views!
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10.0 (2 Reviews)
3 Bedrooms 6 Guests
Ragged Edge Resort & Marina
Fromد.إ.‏948 per night
9.6 (246 Reviews)
1 Bedroom 2 Guests
Anglers Reef Paradise
Fromد.إ.‏1,469 per night
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9.6 (19 Reviews)
2 Bedrooms 6 Guests
The Islands of Islamorada
Fromد.إ.‏2,681 per night
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9.6 (75 Reviews)
1 Bedroom 4 Guests
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
10.0 (124 Reviews)
5 Bedrooms 10 Guests
Anglers Reef Vacation Rental
Fromد.إ.‏1,818 per night
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9.5 (2 Reviews)
2 Bedrooms 6 Guests
Treasure Harbor
Fromد.إ.‏1,219 per night
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9.0 (139 Reviews)
1 Bedroom 2 Guests
Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
10.0 (116 Reviews)
4 Bedrooms 8 Guests
Ragged Edge Resort & Marina
Fromد.إ.‏1,003 per night
9.1 (136 Reviews)
14 Bedrooms 39 Guests
Islander Resort
Fromد.إ.‏2,608 per night
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8.9 (1338 Reviews)
107 Bedrooms 68 Guests
Paradise @ Islamorada
Fromد.إ.‏1,423 per night
9.6 (8 Reviews)
2 Bedrooms 8 Guests
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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8.7 (83 Reviews)
88 Bedrooms 69 Guests
Serenity by the Sea! Anglers Reef with Boat Slip Available!
10.0 (122 Reviews)
2 Bedrooms 6 Guests
Chesapeake Beach Resort
Fromد.إ.‏1,282 per night
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8.5 (768 Reviews)
45 Bedrooms 75 Guests
EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS
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8.0 (3 Reviews)
5 Bedrooms 12 Guests
4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
10.0 (118 Reviews)
4 Bedrooms 8 Guests
Drop Anchor Resort & Marina
Fromد.إ.‏1,325 per night
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7.9 (354 Reviews)
18 Bedrooms 43 Guests
Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
10.0 (117 Reviews)
4 Bedrooms 8 Guests
Little Bay Compound
Fromد.إ.‏59,212 per night
New
6 Bedrooms 18 Guests
Oceanfront Private Cottage!
Fromد.إ.‏989 per night
10.0 (114 Reviews)
1 Bedroom 4 Guests
Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach, plus Den
10.0 (105 Reviews)
2 Bedrooms 6 Guests
Breathtaking ocean views for your Paradise vacations
10.0 (102 Reviews)
2 Bedrooms 8 Guests
Little Bay Prime
Fromد.إ.‏4,036 per night
New
4 Bedrooms 12 Guests
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
10.0 (83 Reviews)
2 Bedrooms 6 Guests
Hidden Gem Duplex in Heart of Islamorada Sleeps 8
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New
4 Bedrooms 8 Guests
Martin Family Fish Camp
Fromد.إ.‏3,026 per night
New
4 Bedrooms 12 Guests
Renovated Anglers Reef 2BR + Sleeper + Ocean Views, Pool, Marina, Sleeps 8
10.0 (72 Reviews)
2 Bedrooms 8 Guests
Oceanfront Islamorada Townhome with Dock and Pool
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New
3 Bedrooms 7 Guests
Anglers Reef Islamorada - 2:2.5, Boat Slip, Pool & Beach
10.0 (56 Reviews)
2 Bedrooms 6 Guests
Oceanfront Keys Escape | Private Beach & Pool | 3 Acres
10.0 (52 Reviews)
3 Bedrooms 8 Guests
Hidden Gem Islamorada | 1st Floor
Fromد.إ.‏2,059 per night
10.0 (44 Reviews)
2 Bedrooms 4 Guests
Venetian Shores Waterfront with Ocean Access, Pool
10.0 (39 Reviews)
3 Bedrooms 8 Guests
Islamorada's Anglers Reef- Remodeled bathrooms-April Special
10.0 (38 Reviews)
2 Bedrooms 6 Guests
Angler's Reef Resort by KeysCaribbean
Fromد.إ.‏1,686 per night
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9.0 (14 Reviews)
2 Bedrooms 4 Guests
The Caribbean Resort
Fromد.إ.‏2,347 per night
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10.0 (166 Reviews)
1 Bedroom 2 Guests
Casa Morada
Fromد.إ.‏2,043 per night
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9.4 (430 Reviews)
1 Bedroom 2 Guests
Oceanfront 4BR Villa | Resort Access + Bunks
10.0 (1 Review)
4 Bedrooms 10 Guests
LIttle Bay Lower
Fromد.إ.‏2,020 per night
New
2 Bedrooms 7 Guests
Luxurious Caribbean 2 Bedroom 2 Bath Home
10.0 (1 Review)
2 Bedrooms 8 Guests
Little Bay Cottage
Fromد.إ.‏2,020 per night
New
2 Bedrooms 4 Guests
Best Place to Stay in Florida! 3 Pet-Friendly Units, Free Breakfast, Parking
10.0 (1 Review)
3 Bedrooms 12 Guests
Little Bay Upper
Fromد.إ.‏1,961 per night
New
2 Bedrooms 6 Guests
Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!
10.0 (1 Review)
3 Bedrooms 12 Guests
Florida Keys Boat Trips Multi Activity
Fromد.إ.‏1,256 per night
New
1 Bedroom 6 Guests
Angler's Reef : Waterfront Beach, Pool, Kayaks & Boat Dock Available
10.0 (1 Review)
2 Bedrooms 6 Guests
La Dolce Vita Villa
Fromد.إ.‏1,223 per night
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New
3 Bedrooms 6 Guests
OCEAN VIEW ANGLERS REEF - POOL, BEACH. Walk or bike to local food + bars
10.0 (1 Review)
2 Bedrooms 5 Guests
Florida Keys Boat Charters
Fromد.إ.‏1,190 per night
New
1 Bedroom 6 Guests
House in Islamorada, in exclusive Venetian Shores.
10.0 (1 Review)
3 Bedrooms 6 Guests
Sunshine Place
Fromد.إ.‏1,109 per night
New
1 Bedroom 3 Guests
3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
10.0 (1 Review)
3 Bedrooms 6 Guests
Beacon Reef 503
Fromد.إ.‏940 per night
New
2 Bedrooms 4 Guests
Beacon Reef 222
Fromد.إ.‏925 per night
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New
2 Bedrooms 4 Guests

About Casai's Private Villas and Holiday Rentals in Windley Key

Discover more than 802 vacation rentals available in Windley Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windley Key.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windley Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windley Key. On average, places to stay near Windley Key offer 663.43 ft², with nightly prices averaging د.إ.‏2,950.

With Casai, finding and comparing holiday rentals in Windley Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Nearby Neighborhood (1)

NeighborhoodProperty Count
Venetian Shores Vacation Rentals in Florida 40