Villa holiday rentals in Grassy Key
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Top-rated villa rentals in Grassy Key
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 Grassy Key
Private villa rentals
Villa in Marathon
4.36 out of 5 average rating, 11 reviewsKey Lime Cottage - Lovely Duck Key Villa, Dip Pool
3–10 Aug
Villa in Marathon
4.61 out of 5 average rating, 46 reviewsParadise Duck Key Villa 2B/1.5B
17–24 Feb
Villa in Marathon
5.0 out of 5 average rating, 6 reviewsTranquil Ocean View Villa with relaxing tiki
13–20 Oct
Villa in Islamorada
5.0 out of 5 average rating, 18 reviewsBayside Villa in Islamorada
26 Oct – 2 Nov
Villa in Marathon
Refreshed & Elevated Indigo Reef Luxury Villa 15
24–31 Aug
Villa in Marathon
The Salty Mermaid 4BR/3BA Anglers at Sombrero Beach with Private Pool and Dockage
3–10 Mar
Villa in Marathon
4.86 out of 5 average rating, 83 reviewsMarina front villa *Family Friendly*
8–15 Apr
Villa in Marathon
4.86 out of 5 average rating, 83 reviewsVilla 5023 on Duck Key BOAT SLIP available
19–26 Jan
Luxury villa rentals
Villa in Marathon
5.0 out of 5 average rating, 3 reviewsVilla Marlin - Perfect Vacation in Florida Keys
15–22 Apr
Villa in Key Largo
4.86 out of 5 average rating, 21 reviewsConch 3-Bedroom Villa
19–26 Jun
Villa in Islamorada
4.64 out of 5 average rating, 25 reviewsCozy 2-bedroom villa with resort amenities
21–28 Dec
Villa in Marathon
4.67 out of 5 average rating, 3 reviewsVilla Sombrero
25 Jan – 1 Feb
Villa in Key Largo
4.79 out of 5 average rating, 68 reviewsOceanfront Villa overlooking the Atlantic
8–15 Nov
Villa in Marathon
Harbor hideaway 50’dock 3Br/2Ba All amenities
14–21 Apr
Villa in Marathon
Canal Front, Tiki Hut w/TV, Private Pool, Beach!
26 Aug – 2 Sep
Villa in Key Colony Beach
Cabana Club Privileges! 4/4 Private Pool, KCB!
12–19 Sep
Villa rentals with a pool
Villa in Duck Key
4.56 out of 5 average rating, 9 reviews2BR water view with private pool, balcony & kayak
22–29 Apr
Villa in Marathon
5.0 out of 5 average rating, 15 reviewsIndigo Reef water view Villa- #1 Guest Favorite
17–24 Nov
Villa in Islamorada
5.0 out of 5 average rating, 27 reviewsAnglers Reef Islamorada
10–17 Oct
Villa in Marathon
4.88 out of 5 average rating, 32 reviewsCanal Front, Tiki Hut, Kayaks, Bikes, Pool, Beach!
17–24 Aug
Villa in Marathon
5.0 out of 5 average rating, 5 reviewsWaterfront Villa (38) w/ sunset views & boat slip
13–20 Jan
Villa in Marathon
4.73 out of 5 average rating, 33 reviewsPrivate Pool and Dock, Canal Front, Bikes, Beach!
5–12 Nov
Villa in Marathon
4.81 out of 5 average rating, 31 reviewsBeautiful 3 bedroom house with loft, pool and dock
15–22 Dec
Villa in Marathon
5.0 out of 5 average rating, 8 reviewsMarlin House (52): Luxury 3/3 Villa w/ Dock, Pool
6–13 Jul
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