Holiday rentals in Florida Keys
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Top-rated holiday rentals in Florida Keys
Guests agree: these stays are highly rated for location, cleanliness and more.
Guest suite in Homestead
4.9 out of 5 average rating, 305 reviewsHoneymoon Suite~Beach essentials & free parking
🌴Come and relax in our clean and cozy private guest suite, nested within a beautiful and safe gated community. Located just north of Key Largo, near Everglades National Park and Biscayne National Park. Whether you plan on exploring the fun city of Miami or enjoy the gorgeous Florida Keys, you will be in a great central location! Our guest suite has a luxurious and comfortable bed, high end amenities and a Smart TV. Everything you need to unwind, relax and recharge after a fun day of exploring! 😴
7–14 Nov
Tiny home in Cutler Bay
4.99 out of 5 average rating, 148 reviewsQuiet tropical Oasis setting with 1 bed and 1 bath
Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.
5–12 Aug
Home in Key West
4.94 out of 5 average rating, 268 reviewsRomantic Retreat - 2 person K Suite, Pvt deck/Spa!
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.
4–11 Aug
Holiday rentals for every style
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Popular amenities for Florida Keys holiday rentals
Other great holiday rentals in Florida Keys
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 81 reviewsTurtle-By-The-Sea: the Best Deal in KCB!
3–10 May
Tiny home in Key Largo
4.98 out of 5 average rating, 57 reviewsOceanfront Lookout Point w/two Kayaks & Deck
4–11 Oct
Houseboat in Key West
4.91 out of 5 average rating, 35 reviewsThe Crystalmarine Suite – Rustic Luxury on the Sea
7–14 Feb
Home in Key Largo
5.0 out of 5 average rating, 44 reviewsThe Paradise 2
2–9 Feb
Home in Marathon
4.97 out of 5 average rating, 31 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
9–16 Nov
Home in Marathon
5.0 out of 5 average rating, 8 reviewsMillion Dollar View
12–19 Oct
Home in Marathon
4.97 out of 5 average rating, 31 reviewsThe Gulf Cottage at Marathon Key
8–15 Jun
Home in Key Colony Beach
4.98 out of 5 average rating, 44 reviewsCaptain’s Quarters Ahoy Mateys! Florida, Keys
1–8 Oct
Home in Key Largo
4.99 out of 5 average rating, 69 reviewsLittle Cottage on an island
17–24 Jun
Apartment in Key West
4.96 out of 5 average rating, 76 reviewsHidden Beach unit 1 The Perfect Place to stay
29 Nov – 6 Dec
Home in Marathon
5.0 out of 5 average rating, 29 reviews100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
23–30 Oct
Home in Marathon
5.0 out of 5 average rating, 19 reviewsParadise in the Keys
17–24 Jan
Destinations to explore
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- West Palm Beach Holiday rentals
- Varadero Holiday rentals
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