Vacation Rentals with Pool in Florida Keys Beaches, FL: Compare 10+ Sites & Save

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250 Best Vacation Rentals with Pool in Florida Keys Beaches (Starting from $301)

Bungalows Sugarloaf Beach Key West - Hammock House
Bungalows Sugarloaf Beach Key West - Hammock House
House
Sugarloaf Shores, FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1695
Average price / night
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The Lighthouse - Beach Houses Key West
The Lighthouse - Beach Houses Key West
House
Upper Sugarloaf Key, FL, 33042, United States
1.0k from Florida Keys Beaches center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
9.6

Exceptional

11 reviews

$1893
Average price / night
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Bungalows Beach Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$1395
Average price / night
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SUGARLOAF OASIS - heated pool & boat dock
SUGARLOAF OASIS - heated pool & boat dock
House
Sugarloaf Key, FL, 33042, United States
2.4k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom8 Guests
New to Booking
$562
Average price / night
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Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom8 Guests
New to Booking
$1198
Average price / night
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Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront
Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront
House
Sugarloaf Key, FL, 33042, United States
2.4k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms10 Guests
9.8

Exceptional

56 reviews

$610
Average price / night
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Bungalows Beach Key West - Hemingway
Bungalows Beach Key West - Hemingway
House
FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$1104
Average price / night
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Tropical paradise on canal in Lower Keys-pool, tiki, firepit, dock, dog friendly
Tropical paradise on canal in Lower Keys-pool, tiki, firepit, dock, dog friendly
House
Summerland Key, FL, 33042, United States
2.6k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$332
Average price / night
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Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
4.8k from Florida Keys Beaches center

Accommodations, Pools, Parking, Lodges, Cabins, Lodgings, Places to stay, Accessible hotels

13 Bedrooms10 Guests
7.4

Good

552 reviews

$313
Average price / night
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Sunset Views • Heated Pool • Fire Pit • Sleeps 6
Sunset Views • Heated Pool • Fire Pit • Sleeps 6
House
Sugarloaf Key, FL, 33042, United States
2.7k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
New to Booking
$428
Average price / night
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Villa of the Setting Sun
Villa of the Setting Sun
House
Florida Keys Beaches, Florida, USA
6.4k from Florida Keys Beaches center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

4 Bedrooms8 Guests
8.0

Good

1 reviews

$2804
Average price / night
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Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool
Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool
House
Summerland Key, FL, 33042, United States
3.0k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$1035
Average price / night
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Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages
House
Summerland Key, FL, USA
6.7k from Florida Keys Beaches center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

20 Bedrooms12 Guests
9.0

Fabulous

314 reviews

$458
Average price / night
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Swimming Pool / Boat Dock / Close to Key West
Swimming Pool / Boat Dock / Close to Key West
House
Sugarloaf, FL, 33042, United States
3.0k from Florida Keys Beaches center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
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Newly built home in Cudjoe Key
Newly built home in Cudjoe Key
House
Cudjoe Key, FL, USA
7.6k from Florida Keys Beaches center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms7 Guests
New to Booking
$583
Average price / night
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$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
House
Sugarloaf Key, FL, 33042, United States
3.0k from Florida Keys Beaches center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$552
Average price / night
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Luxury OceanView Friendly Villa Near Key West
Luxury OceanView Friendly Villa Near Key West
Villa
Florida Keys Beaches, Florida, USA
8.2k from Florida Keys Beaches center

Pool, Parking, Laundry, Hot Tub, Balcony/Terrace, Pet Friendly, Kitchen

4 Bedrooms10 Guests
1.0

Review score

1 reviews

$804
Average price / night
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**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
House
Sugarloaf Key, FL, 33042, United States
3.6k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$638
Average price / night
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Ocean View with Pool, 4 bedroom Vila Near Key West
Ocean View with Pool, 4 bedroom Vila Near Key West
Villa
Cudjoe Key, FL, USA
8.3k from Florida Keys Beaches center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$810
Average price / night
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Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!
House
Sugarloaf, FL, 33042, United States
3.8k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

4 Bedrooms10 Guests
9.8

Exceptional

14 reviews

$641
Average price / night
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Parrotfish Pointe
Parrotfish Pointe
House
Cudjoe Key, FL, USA
8.5k from Florida Keys Beaches center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

3 Bedrooms6 Guests
New to Booking
$301
Average price / night
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PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
House
Summerland Key, FL, 33042, United States
3.9k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$384
Average price / night
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Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Dining & Pet Friendly!
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Dining & Pet Friendly!
House
Sugarloaf Key, FL, 33042, United States
4.0k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$383
Average price / night
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Lock in summer months. For up to date availability\n510-381-5000
Lock in summer months. For up to date availability\n510-381-5000
House
Sugarloaf, FL, 33042, United States
4.4k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$402
Average price / night
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Sunset Bay: Spacious 5BR Getaway, Dockage, Heated Pool, Dog OK, Stunning Views & Minutes to Key West
Sunset Bay: Spacious 5BR Getaway, Dockage, Heated Pool, Dog OK, Stunning Views & Minutes to Key West
House
Saddlebunch Key, FL, 33040, United States
4.5k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, Kitchen, Microwave

5 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$419
Average price / night
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Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount
Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount
House
Key West, FL, 33040, United States
4.5k from Florida Keys Beaches center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
9.4

Superb

15 reviews

$346
Average price / night
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Luxurious Oceanfront 5BR Property with heated Pool & Waterfall
Luxurious Oceanfront 5BR Property with heated Pool & Waterfall
House
Key West, FL, 33040, United States
4.5k from Florida Keys Beaches center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
10.0

Exceptional

9 reviews

$851
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Florida Keys Beaches.

Where to stay in Florida Keys Beaches? Best neighborhoods & areas

Florida Keys Beaches Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 250 verified vacation rentals with a pool in Florida Keys Beaches. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Florida Keys Beaches vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $301 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Florida Keys Beaches offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Florida Keys Beaches welcome pets. Currently, 38 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Florida Keys Beaches often include additional outdoor features such as Pool, Balcony/Terrace, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Florida Keys Beaches offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.