Villas and Vaction Homes in Florida Keys, FL

45151 Villas and Vacation Homes in Florida Keys, FL

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Florida Keys, FL
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Best villa offers in Florida Keys, FL

Key Largo Cottages W/ Free Sailboat, Kayaks + More - Florida Keys, FL
Florida Keys, FL
07/21 – 07/30
$333/nighttotal: $2997 (9 )

Key Largo Cottages W/ Free Sailboat, Kayaks + More

1 2
cottage, Key Largo
Mermaid Cottage is centrally located in Key Largo, nestled between the Jungle and Manatee cottages, offering proximity to the Caribbean Club Bar and Christ of the Abyss statue, just 500 feet from the coastline making it an ideal beach house.
This 220 square foot villa accommodates up to 4 guests with a queen-size bed and bunk beds, featuring a fully equipped kitchenette, a private bathroom with a tiled shower, and access to a shared common area with a gas grill and picnic table, perfect for exploring nearby John Pennekamp Coral Reef State Park.
173 M² House ∙ 3 Bedrooms ∙ 8 Guests - Florida Keys, FL
10 1 review
Florida Keys, FL
05/08 – 05/22
$231/nighttotal: $3234 (14 )

173 M² House ∙ 3 Bedrooms ∙ 8 Guests

3 2
house, Marathon
Directly overlooking a marina, this townhome in Marathon's Bonefish Yacht Club is located just 0.2 miles from Coco Plum Beach, offering direct fishing access from the dock.
This 1850 sq ft villa comfortably accommodates 8 guests with 3 bedrooms and 3 bathrooms, featuring a gourmet kitchen, air conditioning, a swimming pool, spa, fitness center, and parking, making it an ideal holiday home.
Sea Shell Cottage, Sleeps 2 - Escape The Cold; Our Pool Is Heated! - Florida Keys, FL
9.8 36 reviews
Florida Keys, FL
07/21 – 07/30
$214/nighttotal: $1926 (9 )

Sea Shell Cottage, Sleeps 2 - Escape The Cold; Our Pool Is Heated!

1 2
cottage, Cudjoe Key
The Sea Shell Cottage UNIT #2 is located on Summerland Key, 25 miles from Key West's dining and nightlife, and a 2-minute walk to Tonio's Seafood Shack & Tiki Bar, offering convenient access to boat ramps and nearby marinas.
This welcoming 1-bedroom, 1-bathroom cottage accommodates 2 guests and features an efficiency kitchen, air conditioning, WiFi, and complimentary use of resort amenities including a communal outdoor pool and gas grill, making it an ideal holiday home for exploring Bahia Honda State Park, just a 15-minute drive away.
Spacious Villa  4-bedroom With Heated Pool - Florida Keys, FL
9.6 7 reviews
Florida Keys, FL
03/28 – 04/18
$476/nighttotal: $9996 (21 )

Spacious Villa 4-bedroom With Heated Pool

4 2
house, The Crossings
Located in Miami's established The Crossings neighborhood, this 4-bedroom house offers convenient access to Dadeland Mall, Dolphin Mall, and Zoo Miami, with Brickell and South Beach approximately 20-30 minutes away.
This welcoming villa features a large swimming pool and patio area, perfect for groups, along with a fully equipped kitchen and modern amenities including Smart TVs, accommodating up to 11 guests.
Villa Del Sol - Sunset Views, Kayaks, 2/2.5 - Florida Keys, FL
10 3 reviews
Florida Keys, FL
04/24 – 04/26
$660/nighttotal: $1320 (2 )

Villa Del Sol - Sunset Views, Kayaks, 2/2.5

2 2
house, Duck Key
Offering breathtaking sunset views and endless vistas of turquoise waters, this waterfront villa is precisely located in Duck Key, providing quick access to Marathon (15 miles), Sombrero Beach (20 miles), and Seven Mile Bridge (25 miles).
This nearly 900 sq. ft. holiday home accommodates up to 6 guests with 2 bedrooms featuring ensuite bathrooms and a queen sofa bed, complemented by three kayaks for exploring the surrounding waters.
Casa Del Mar- Luxury Waterfront Pool Home, 45' Dock - Florida Keys, FL
Florida Keys, FL
05/08 – 05/22
$824/nighttotal: $11536 (14 )

Casa Del Mar- Luxury Waterfront Pool Home, 45' Dock

4 2
house, Marathon
Casa Del Mar is a luxury waterfront pool home in Marathon, offering a prime location with a 45' dock, just 3.5 miles from Florida Keys Aquarium Encounters and Seven Mile Bridge.
This exclusive villa, boasting 1990 square feet of living space, features 4 bedrooms and 4 bathrooms to accommodate up to 19 guests, complete with a private swimming pool, spa, fitness center, and on-site concierge for a comfortable holiday home experience.
Truly Sitting Right On The Ocean. Ocean's Edge Has Forever Ocean Views. - Florida Keys, FL
10 8 reviews
Florida Keys, FL
08/20 – 08/24
$454/nighttotal: $1816 (4 )

Truly Sitting Right On The Ocean. Ocean's Edge Has Forever Ocean Views.

2 4
cottage, Cudjoe Key
Directly on the Atlantic Ocean with sunrise views, this cottage is located on Summerland Key in the Florida Keys, offering convenient 52-foot seawall boat docking and proximity to Venture and Out Keys.
This 900 sq ft holiday home accommodates up to 6 guests and provides access to Venture Out Resort's amenities, including a large pool, hot tub, tennis, pickleball, and a playground, making it an ideal beach house for exploring nearby Florida Keys Beaches and Bahia Honda State Park.
Sunny Hideaway - Venture Out Unit 276 - Florida Keys, FL
9.4 6 reviews
Florida Keys, FL
03/27 – 04/02
$387/nighttotal: $2322 (6 )

Sunny Hideaway - Venture Out Unit 276

2 2
apartment, Cudjoe Key
This waterfront apartment in Summerland Key offers direct access to open water, featuring a 35' concrete seawall for boat docking, a swim ladder, and a fish table, all within walking distance to the community pool and marina.
Boasting 850 square feet, this welcoming holiday home accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, complemented by a private master bath, an open floor plan with high ceilings, and a covered porch perfect for outdoor relaxation, while complimentary wireless internet is available in the rec hall.
Indigo Reef #23 - Lionfish Lodge- Luxury Waterfront Villa, 31' Dock - Florida Keys, FL
Florida Keys, FL
03/21 – 03/28
$425/nighttotal: $2975 (7 )

Indigo Reef #23 - Lionfish Lodge- Luxury Waterfront Villa, 31' Dock

3 2
house, Marathon
This luxury waterfront villa in Marathon offers sea views and a private 31' dock, situated an 8-minute walk from Florida Keys Aquarium Encounters and 1 mile from Captain Hook S Marina Dive Center.
Boasting 1600 square feet with 3 bedrooms and 2 bathrooms, this holiday home accommodates up to 15 guests and features a spa, swimming pool, fitness center, and on-site massage services.
Island Time - Luxury Waterfront Pool Home, 32' Dock - Florida Keys, FL
Florida Keys, FL
05/08 – 05/22
$508/nighttotal: $7112 (14 )

Island Time - Luxury Waterfront Pool Home, 32' Dock

3 2
house, Marathon
Located in Marathon, this waterfront villa offers direct sea views and a private dock, situated a mere 6-minute walk from Florida Keys Aquarium Encounters and 0.9 miles from Captain Hook S Marina Dive Center.
This 1390 sq ft holiday home accommodates up to 15 guests across 3 bedrooms and 2 bathrooms, featuring a private swimming pool, spa, fitness center, and fully equipped kitchen with free WiFi, making it an ideal beach house for your getaway.
Cozy 3-bedroom Townhome Inhomestead , Near Keys, With Ac, Full Kitchen , Wifi - Florida Keys, FL
9.2 12 reviews
Florida Keys, FL
03/28 – 04/18
$619/nighttotal: $12999 (21 )

Cozy 3-bedroom Townhome Inhomestead , Near Keys, With Ac, Full Kitchen , Wifi

4 2
apartment, Homestead
Perfectly situated in Homestead, this townhome offers convenient access to explore the Florida Keys, Miami Beach, and Zoo Miami, placing you within reach of major attractions.
This expansive 1600 sq ft villa comfortably accommodates 8 guests with 4 bedrooms and 2 bathrooms, featuring a jetted bathtub and bidet, plus on-site amenities like AC, WiFi, and a fitness room.
Adventures In Sombrero - Waterfron Pool Home, 26' Dock - Florida Keys, FL
Florida Keys, FL
03/21 – 03/28
$507/nighttotal: $3549 (7 )

Adventures In Sombrero - Waterfron Pool Home, 26' Dock

1 2
house, Marathon
Directly on the waterfront in Marathon, this welcoming villa offers private 26' dock access, positioning you just 1.3 miles from the sandy shores of Sombrero Beach and 3.5 miles from Florida Keys Aquarium Encounters.
This spacious 4-bedroom holiday home, boasting 1880 square feet of living space, comfortably accommodates up to 19 guests with amenities including a private swimming pool, fully equipped kitchen, and complimentary WiFi.

Villas and Vacation Homes with Pool in Florida Keys, FL

Among the 45151 villas in Florida Keys, FL here are the 8 best villas with pool

Yellowtail Island Retreat - 3br Keys Home W/ Pool, Dockage, Porch & Canal Access - Florida Keys, FL
10 68 reviews
Florida Keys, FL
03/21 – 03/28
$543/nighttotal: $3801 (7 )

Yellowtail Island Retreat - 3br Keys Home W/ Pool, Dockage, Porch & Canal Access

3 2
apartment, Marathon
Boasting a prime waterfront location on a clear, flow-through canal in Marathon, this exceptional villa offers direct access to boating and fishing, situated just a short drive from the Crane Point Museum and Nature Center and the Marathon Air Museum.
This expansive 1500 sq ft holiday home accommodates up to 8 guests with 3 bedrooms and 2 bathrooms, featuring a private heated and chilled pool, a 30-foot private dockage, a fully equipped granite kitchen, and a wrap-around porch with tranquil water views, making it an ideal beach house for your next getaway.
Time To Chill - 3/3 Kawama Townhouse With Free Golf Cart, Kayaks & Bicycles. - Florida Keys, FL
9.6 83 reviews
Florida Keys, FL
06/15 – 06/19
$558/nighttotal: $2232 (4 )

Time To Chill - 3/3 Kawama Townhouse With Free Golf Cart, Kayaks & Bicycles.

3 8
apartment, Key Largo
Located in Key Largo's Kawama district, this three-story townhouse is just steps from the oceanfront and a short drive to John Pennekamp Coral Reef State Park and Jimmy Johnson's Big Chill.
This family-friendly apartment offers 1500 square feet of living space, accommodating up to 8 guests with 3 bedrooms and 3 bathrooms, and features a private terrace, swimming pool, and complimentary golf cart, bicycles, and kayaks for exploring the area.
Kawama N2 In Key Largo, Beach, Lagoon, Pools, Tennis, Free Bikes And Canoes - Florida Keys, FL
9.0 4 reviews
Florida Keys, FL
03/23 – 03/25
$863/nighttotal: $1726 (2 )

Kawama N2 In Key Largo, Beach, Lagoon, Pools, Tennis, Free Bikes And Canoes

3 2
house, Key Largo
KAWAMA N2 offers direct access to beach and lagoon amenities in Key Largo, situated just 4.5 miles from John Pennekamp State Park and 4.6 miles from Dolphin Cove.
This exceptional villa, a perfect holiday home, boasts 3 bedrooms, accommodates up to 15 guests, and features on-site pools, complimentary bikes, canoes, and a balcony for outdoor enjoyment.
Palm Villa - Florida Keys, FL
8.6 243 reviews
Florida Keys, FL
05/31 – 06/06
$396/nighttotal: $2376 (6 )

Palm Villa

2 2
house, Duck Key
Palm Villa is located in Duck Key, 8.6 miles from Florida Keys Aquarium Encounters and 21 miles from Upper Matecumbe Key.
This welcoming villa features 930 square feet of living space with 2 bedrooms and 2 bathrooms, offering a private terrace, swimming pool, on-site restaurant, and activities like cycling and a children's playground.
Canal-side Charisma - Florida Keys, FL
9.0 65 reviews
Florida Keys, FL
06/11 – 06/18
$455/nighttotal: $3185 (7 )

Canal-side Charisma

2 4
house, Key Colony Beach
Canal-side Charisma is a canal-side villa in Key Colony Beach, located 2.1 miles from Florida Keys Aquarium Encounters and an 11-minute walk from Sunset Park Beach.
This welcoming 1240 square foot, air-conditioned holiday home offers 2 bedrooms, accommodates up to 6 guests, and features a private hot tub, a terrace with canal views, a well-equipped kitchen with a dishwasher, and an on-site restaurant with a pool.
Paradise Palms - Luxury Waterfront Pool Home, 40' Dock - Florida Keys, FL
Florida Keys, FL
05/08 – 05/22
$673/nighttotal: $9422 (14 )

Paradise Palms - Luxury Waterfront Pool Home, 40' Dock

3 2
house, Marathon
This luxury waterfront villa in Marathon is a 14-minute walk to Coco Plum Beach and 1.2 miles from A Deep Blue Dive Center.
Offering 2640 square feet of living space, this 3-bedroom, 3-bathroom holiday home accommodates up to 15 guests with amenities including a private pool, a 40' dock, a spa center, and on-site massage services.
Captain Joe's Kcb Beach 5-star Getaway Kcb#5 - Florida Keys, FL
9.8 48 reviews
Florida Keys, FL
03/21 – 03/28
$490/nighttotal: $3430 (7 )

Captain Joe's Kcb Beach 5-star Getaway Kcb#5

3 2
apartment, Key Colony Beach
Located in Key Colony Beach, this waterfront vacation home offers direct ocean/bay access and a private dock, just a 5-minute walk to the exclusive Private Cabana Club with its sandy beach, Jacuzzi, and Olympic heated pool.
This 1580 sq ft villa comfortably accommodates up to 7 guests with 3 bedrooms and 2 bathrooms, featuring ground-floor accessibility, air conditioning, a swimming pool, and parking, making it an ideal holiday home for exploring nearby attractions like Captain Hooks Marina, Florida Keys Country Club, Sombrero Beach, and Curry Hammock State Park.
Villa Devera: Marinaview •Pools •Private Terraces - Florida Keys, FL
10 3 reviews
Florida Keys, FL
06/15 – 06/19
$906/nighttotal: $3624 (4 )

Villa Devera: Marinaview •Pools •Private Terraces

3 8
house, Key Largo
Villa DeVera, a waterfront villa within Key Largo's exclusive Mariner's Club, offers direct marina views and is located just 0.5 miles from John Pennekamp Coral Reef State Park, ideal for snorkeling and diving adventures.
This newly renovated, family-friendly retreat accommodates up to 8 guests across 3 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, private terraces, access to 2 heated pools, hot tubs, a fitness center, and a deep-water marina accommodating boats up to 60 feet.

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