Holiday rentals in Monroe County
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Top-rated holiday rentals in Monroe County
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
Bungalow in Homestead
4.92 out of 5 average rating, 368 reviewsRedlands Bungalow
Newly remodeled bungalow on 2 acres estate. Private entrance, yard with privacy fence and patio with gas grill and dining, all detached from main house. 10 mins walk to RF Orchids. 15 mins drive to Everglades or Biscayne Ntl Parks, 40 mins to the Keys and 45 mins to Miami and the beaches. Featuring 2 bdrms with superior quality mattress and smart TVs, Netflix included. New bathroom, washer/ dryer. The kitchen is equipped with a cook top, microwave, dishwasher and a full size refrigerator.
13–20 Jun
Holiday rentals for every style
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Popular amenities for Monroe County holiday rentals
Other great holiday rentals in Monroe County
Guest suite in Tavernier
4.98 out of 5 average rating, 245 reviewsIsland Get Away
25 Aug – 1 Sep
Villa in Marathon
4.89 out of 5 average rating, 141 reviewsNew Aqua Lodge 2Beds 1 Bath with Full Kitchens
2–9 Sep
Guest suite in Homestead
4.92 out of 5 average rating, 117 reviewsCozy 1BR guestroom, private entrance, free parking
30 Jun – 7 Jul
Home in Cudjoe Key
4.92 out of 5 average rating, 134 reviewsParadise at Cudjoe Bay
30 May – 6 Jun
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, 43 reviewsThe Paradise 2
2–9 Feb
Tiny home in Miami
4.98 out of 5 average rating, 42 reviewsTropical Tiny Living Experience
5–12 Jun
Tiny home in Big Pine Key
4.8 out of 5 average rating, 88 reviewsBreezy pines 28 foot 5th wheel trailer .
16–23 Oct
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
Guest suite in Miami
4.98 out of 5 average rating, 55 reviewsPeaceful & Private Miami Getaway
30 Jul – 6 Aug
Home in Marathon
4.97 out of 5 average rating, 31 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
9–16 Nov
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
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