Cottage holiday rentals in Florida Keys
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Top-rated cottage rentals in Florida Keys
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Florida Keys
Cottage rentals with a hot tub
Cottage in Fort Lauderdale
4.92 out of 5 average rating, 234 reviewsCentrally Located Private Cottage
25 Mar – 1 Apr
Cottage in Cudjoe Key
4.91 out of 5 average rating, 79 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
31 Mar – 7 Apr
Cottage in Key West
4.82 out of 5 average rating, 22 reviewsDarling of Duval @ Old Town - Adorable Cottage
27 Jun – 4 Jul
Cottage in Fort Lauderdale
5.0 out of 5 average rating, 88 reviewsPrivate Couple’s cottage. Hotub. Beach. Miami
26 Aug – 2 Sep
Cottage in Lazy Lake
4.85 out of 5 average rating, 54 reviewsEnchanting Hideaway - minutes from everything.
2–9 Oct
Cottage in Naples
4.91 out of 5 average rating, 11 reviewsClub Naples Resort Cottage
8–15 Jan
Cottage in Oakland Park
4.8 out of 5 average rating, 243 reviewsTropical Oasis Pool Cottage
5–12 Oct
Cottage in Cudjoe Key
4.61 out of 5 average rating, 94 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
21–28 Jan
Pet-friendly cottage rentals
Cottage in Islamorada
4.94 out of 5 average rating, 16 reviewsWaterfront Cottage Walk to World Famous Lorelei
23–30 Nov
Cottage in Key Largo
4.96 out of 5 average rating, 57 reviews2 BR with private Tiki Boat dock for 25' boat max
12–19 Dec
Cottage in Key Largo
4.94 out of 5 average rating, 33 reviewsSpacious cottage in the heart of the keys
3–10 Jan
Cottage in Naples
4.85 out of 5 average rating, 55 reviewsCheerful 2 Bedroom Home in Naples, FL
15–22 Jul
Cottage in Naples
5.0 out of 5 average rating, 12 reviewsCozyCove
9–16 Oct
Cottage in Miami
4.92 out of 5 average rating, 12 reviewsCozy cottage garden & parking
23–30 Jun
Cottage in Coral Gables
5.0 out of 5 average rating, 38 reviewsNew Modern Near Airport - Cozy Very Clean
29 Nov – 6 Dec
Cottage in Miami
4.91 out of 5 average rating, 70 reviewsCottage-Private Gated Estate w/heated Pool Near UM
17–24 Oct
Private cottage rentals
Cottage in Goodland
4.9 out of 5 average rating, 221 reviewsQuiet Olde Florida Cottage on the Bay
3–10 Apr
Cottage in Naples
4.96 out of 5 average rating, 135 reviewsHistoric Coral Cottage in the Heart of Old Naples
26 Jul – 2 Aug
Cottage in Miami
4.87 out of 5 average rating, 251 reviewsRuben’s Place
3–10 Oct
Cottage in Naples
5.0 out of 5 average rating, 184 reviewsCoastal Vibes Cottage Pickleball Ct Mile to Beach
19–26 Feb
Cottage in Hollywood
5.0 out of 5 average rating, 102 reviewsCozy beach cottage steps away from Hollywood Beach
8–15 Jan
Cottage in Fort Lauderdale
4.83 out of 5 average rating, 457 reviewsHistoric Renovated Cottage w/ Private Heated Pool!
8–15 Sep
Cottage in Key Largo
4.98 out of 5 average rating, 51 reviewsOceanfront Paradise with Amazing View!
1–8 Oct
Cottage in Key Largo
4.9 out of 5 average rating, 49 reviewsTHE PARADISE
7–14 Oct
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
- Havana Holiday rentals
- Nassau Holiday rentals
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Cottage rentals Miami
- Cottage rentals Florida
- Cottage rentals Fort Lauderdale
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