Villa holiday rentals in Florida Keys
Find and book unique villas on Airbnb
Top-rated villa rentals in Florida Keys
Guests agree: these villas 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 villa rentals in Florida Keys
Private villa rentals
Villa in Duck Key
5.0 out of 5 average rating, 49 reviewsDuck Key *Bliss* Private Pool & Patio
22–29 Sep
Villa in Duck Key
4.86 out of 5 average rating, 21 reviewsFamily Friendly Sunset Oasis!
16–23 May
Villa in Duck Key
4.82 out of 5 average rating, 49 reviewsVilla 5034 on Duck Key BOAT SLIP available
5–12 Oct
Villa in Duck Key
4.98 out of 5 average rating, 59 reviewsWaterfront Island Escape with Private Plunge Pool
29 Aug – 5 Sep
Villa in Marathon
4.95 out of 5 average rating, 56 reviewsVilla in Paradise. Plunge pool. Middle of the Keys
15–22 Jan
Villa in Key Colony Beach
5.0 out of 5 average rating, 13 reviewsKeys Hideaway Completely Remodeled w/ Cabana Club
28 Nov – 5 Dec
Villa in Marco Island
4.88 out of 5 average rating, 48 reviewsBlue Marlin * a space where memories are made!
1–8 Apr
Villa in Key Colony Beach
5.0 out of 5 average rating, 9 reviewsFabulous Canal Front Villa, Private Pool in KCB!
2–9 Oct
Luxury villa rentals
Villa in Hollywood
4.97 out of 5 average rating, 151 reviewsSpectacular 5BR/5BA Villa in Hollywood Lakes
9–16 Feb
Villa in Miami
4.96 out of 5 average rating, 111 reviewsVilla Tulum Miami: Tropical Backyard Oasis
11–18 Jul
Villa in Hollywood
4.96 out of 5 average rating, 137 reviewsVOTED#1 VILLA-OVERSIZED POOL/B-BALL CT MIAMI/FLL
23–30 Oct
Villa in Miami
4.84 out of 5 average rating, 37 reviewsVilla Azur- Salt Water Heated Pool-BKT Court
22–29 Sep
Villa in Miami
4.98 out of 5 average rating, 47 reviewsPrime Brickell Villa: Huge Outdoor w/ Pool+Kitchen
25 May – 1 Jun
Villa in North Bay Village
4.87 out of 5 average rating, 23 reviews☆TROPICAL Villa with POOL ☆Private Island☆
30 Sep – 7 Oct
Villa in Miami
5.0 out of 5 average rating, 79 reviewsMiami Mansion Beach | Heated Pool | Basketball
12–19 Sep
Villa in Marathon
5.0 out of 5 average rating, 9 reviewsWaterfront Home w/Dock, Pool, Bikes & SO MUCH MORE
7–14 Jun
Villa rentals with a pool
Villa in Miami
5.0 out of 5 average rating, 21 reviewsModern Villa in Miami “ Villa Vetter “
9–16 Aug
Villa in Oakland Park
4.99 out of 5 average rating, 88 reviewsThe Jungle House- Heated Pool + Tanning Ledge
16–23 Sep
Villa in Miami
4.94 out of 5 average rating, 98 reviewsNEW! "Villa Paradise" ~ Lux Gem ~ Pool ~ Game Room
27 Jan – 3 Feb
Villa in Marco Island
4.96 out of 5 average rating, 27 reviewsVilla Cecilia ★ 0.2 Miles from the Beach
7–14 Oct
Villa in Pompano Beach
5.0 out of 5 average rating, 82 reviewsIsland Time Waterfront Oasis! Boat rental/HTD Pool
25 Sep – 2 Oct
Villa in Miami
4.96 out of 5 average rating, 55 reviews6BR Villa: King Bed Pool & Sprawling Private Oasis
23–30 Jul
Villa in Key Largo
4.92 out of 5 average rating, 100 reviewsKawama Yacht Club and Molasses Reef Marine
9–16 Nov
Villa in Naples
4.96 out of 5 average rating, 23 reviewsLovely 3-bed villa, Briarwood neighborhood, Naples
17–24 Sep
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
- Villa rentals Miami
- Villa rentals United States
- Villa rentals Miami Beach
- Villa rentals Florida
- Villa rentals Fort Lauderdale
- House rentals Florida Keys
- Hotel rentals Florida Keys
- Townhouse rentals Florida Keys
- Monthly Rentals Florida Keys
- Rentals with beach access Florida Keys
- Apartment rentals Florida Keys
- Motorhome rentals Florida Keys
- Pet-friendly rentals Florida Keys
- Houseboat rentals Florida Keys
- Rentals with an accessible-height bed Florida Keys
- Family-friendly rentals Florida Keys
- Tiny house rentals Florida Keys
- Rentals with an EV charger Florida Keys
- Rentals with a washing machine and dryer Florida Keys
- Guest house rentals Florida Keys
- Rentals with an accessible-height toilet Florida Keys
- Smoking-friendly rentals Florida Keys
- Beach house rentals Florida Keys
- Flat rentals Florida Keys
- Wheelchair-accessible rentals Florida Keys
- Resort rentals Florida Keys
- Bungalow rentals Florida Keys
- Bed and breakfasts Florida Keys
- Rentals with a sauna Florida Keys
- Beach apartment rentals Florida Keys
- Boat rentals Florida Keys
- Family-friendly rentals Florida Keys
- Rentals with outdoor seating Florida Keys
- Mansion rentals Florida Keys
- Rentals with a cinema Florida Keys
- Fitness-friendly rentals Florida Keys
- Rentals with lake access Florida Keys
- Rentals with pools Florida Keys
- Serviced apartment rentals Florida Keys
- Rentals with a patio Florida Keys
- Campsite rentals Florida Keys
- Rentals with a firepit Florida Keys
- Private suite rentals Florida Keys
- Boutique hotel rentals Florida Keys
- Beachfront rentals Florida Keys
- Rentals with breakfast Florida Keys
- Cottage rentals Florida Keys
- Rentals with a hot tub Florida Keys
- Rentals with a fireplace Florida Keys
- Waterfront rentals Florida Keys
- Rentals with a kayak Florida Keys
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
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- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom