House holiday rentals in Monroe County
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Top-rated house rentals in Monroe County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Monroe County
House rentals with a pool
Home in Key Largo
4.97 out of 5 average rating, 110 reviewsTiny Home on Waterfront | Bay Views | Deck | Pool
5–12 Jan
Home in Key Largo
4.9 out of 5 average rating, 127 reviewsBlue House Marine in Key Largo
14–21 Sep
Home in Key Colony Beach
4.81 out of 5 average rating, 132 reviewsWaterview from three sides, Cabana Club, 30' Docks
10–17 Jan
Home in Cudjoe Key
4.81 out of 5 average rating, 222 reviewsOCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
22–29 Aug
Home in Miami
5.0 out of 5 average rating, 239 reviewsModern,spacious Retreat !Salt water,heated pool!
22–29 Oct
Home in Key Largo
5.0 out of 5 average rating, 50 reviewsThe Paradise 2
3–10 Apr
Home in Cudjoe Key
4.87 out of 5 average rating, 46 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
18–25 Oct
Home in Marathon
4.97 out of 5 average rating, 33 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
29 Mar – 5 Apr
Weekly house rentals
Home in Marathon
4.97 out of 5 average rating, 35 reviewsThe Gulf Cottage at Marathon Key
25 Jul – 1 Aug
Home in Marathon
5.0 out of 5 average rating, 15 reviewsFlorida Keys Oceanside Utopia
9–16 Jul
Home in Key Largo
4.99 out of 5 average rating, 75 reviewsLittle Cottage on an island
26 Jul – 2 Aug
Home in Upper Sugarloaf Key
4.87 out of 5 average rating, 46 reviewsBungalows at Sugarloaf Beach - The Lighthouse
21–28 Feb
Home in Key Colony Beach
5.0 out of 5 average rating, 96 reviewsABeachBungalow-60’dock w/ access to pool and beach
26 Apr – 3 May
Home in Marathon
5.0 out of 5 average rating, 9 reviewsOceanfront *PARADiSE* Amazing views, pool, dock
1–8 Mar
Home in Key Largo
5.0 out of 5 average rating, 15 reviewsPrivate 1 Acre House~Private Beach~Tiki Hut~Dock
7–14 Sep
Home in Key Largo
4.93 out of 5 average rating, 15 reviewsKeys Paradise 3/3 Waterfront, Jacuzzi, Kayaks+More
27 Dec – 3 Jan
Private house rentals
Home in Miami
5.0 out of 5 average rating, 17 reviewsSerene Seas Studio in Miami.
30 Jul – 6 Aug
Home in Cudjoe Key
4.88 out of 5 average rating, 25 reviewsWhite Vacation Home. Free cancellation see details
16–23 Nov
Home in Key Colony Beach
4.98 out of 5 average rating, 51 reviewsCaptain’s Quarters Ahoy Mateys! Florida, Keys
29 Mar – 5 Apr
Home in Cudjoe Key
5.0 out of 5 average rating, 23 reviewsParadise in Cudjoe! Perfect Family Home!
4–11 Oct
Home in Marathon
5.0 out of 5 average rating, 7 reviewsSalty kisses beach house
18–25 Aug
Home in Marathon
4.9 out of 5 average rating, 40 reviewsMarathon Beach House
1–8 Nov
Home in Islamorada
4.96 out of 5 average rating, 57 reviewsTropical Getaway 3/3 with 100’ boat dock and pool
1–8 Oct
Home in Homestead
4.94 out of 5 average rating, 97 reviewsWelcome to Waltonhurst
29 Aug – 5 Sep
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