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Holiday rentals in Middle Keys

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Top-rated holiday rentals in Middle Keys

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Key West
Romantic 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.
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Guest favourite
Flat in Key West
Bella Vita: 1B/1B Condo for 2 Just Steps off Duval
1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.
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Guest favourite
Apartment in Key West
Large 2/2 Waterfront Condo Great View Pool & Dock
Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grill, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).
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Popular amenities for Middle Keys holiday rentals

Other great holiday rentals in Middle Keys

Guest favourite
Guest house in Key West
Old Town - Room Opens to Pool and Garden
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Guest favourite
Holiday home in Key West
Historic Cigar House. 3rd floor Suite W/Kitchen
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Guest favourite
Tiny home in Key West
Modern studio half block from Duval with parking
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Guest favourite
Home in Key West
Mango Tree Key West Cottage
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Guest favourite
Bungalow in Key West
Atlantis House's Banyan Suite-voted top 25 in USA
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Superhost
Apartment in Key West
Ocean front 1BR/1BA Suite w/ kitchen & living rm
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Guest favourite
Apartment in Key West
Hidden Beach unit 1 The Perfect Place to stay
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Guest favourite
Apartment in Key West
*Come to my Deck for a time you won't Forget!
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Guest favourite
Home in Key West
Gone Coastal
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Guest favourite
Townhouse in Key West
The Flamingo's Nest - Home away from home!
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Superhost
Flat in Key West
Old Town Studio Apartment • Walk Everywhere!
Individual Host
Superhost
Cottage in Key West
Old Town home a short walk to Duval/Couples Oasis
Individual Host

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