Vacation Rentals with Pool in Higgs Beach, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Higgs Beach

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1469 Best Vacation Rentals with Pool in Higgs Beach (Starting from $225)

Casa Atlantic
Casa Atlantic
House
Key West, FL, USA
0.3k from Higgs Beach center

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

3 Bedrooms9 Guests
8.0

Good

1 reviews

$536
Average price / night
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Conch Keys | Private Pool & Outdoor Bar Paradise!
Conch Keys | Private Pool & Outdoor Bar Paradise!
House
Key West, FL, 33040, United States
0.3k from Higgs Beach center

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

2 Bedrooms4 Guests
New to Booking
$245
Average price / night
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Casa de Sunshine
Casa de Sunshine
House
Key West, FL, USA
0.4k from Higgs Beach center

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

2 Bedrooms4 Guests
New to Booking
$358
Average price / night
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Key West, FL - Ocean Front - Coconut Beach Resort
Key West, FL - Ocean Front - Coconut Beach Resort
Condo
Key West, FL, 33040, United States
0.3k from Higgs Beach center

AC, Balcony, Dryer, Extra Bed, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$803
Average price / night
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Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
0.4k from Higgs Beach center

Accommodations, Pools, Resorts, Parking, Spa, Romantic, Pet-friendly, 5-star, Lodgings

27 Bedrooms76 Guests
7.6

Good

261 reviews

$416
Average price / night
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Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking
Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking
House
Key West, FL, 33040, United States
0.4k from Higgs Beach center

AC, Heater, Internet, Laundry, Living Area, Pool

2 Bedrooms6 Guests
9.2

Superb

11 reviews

$821
Average price / night
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Sunshine Drive
Sunshine Drive
House
Key West, FL, USA
0.4k from Higgs Beach center

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

3 Bedrooms10 Guests
New to Booking
$391
Average price / night
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Plantation Tropicale by Last Key Realty
Plantation Tropicale by Last Key Realty
House
Key West, FL, USA
0.5k from Higgs Beach center

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

5 Bedrooms12 Guests
New to Booking
$2964
Average price / night
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**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
House
Key West, FL, 33040, United States
0.4k from Higgs Beach center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$378
Average price / night
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Flagler Station
Flagler Station
House
Key West, FL, USA
0.6k from Higgs Beach center

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

3 Bedrooms6 Guests
New to Booking
$408
Average price / night
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Flirty Flamingo Key West
Flirty Flamingo Key West
House
Key West, FL, 33040, United States
0.4k from Higgs Beach center

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

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$444
Average price / night
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Poolside Paradise Tropical Village
Poolside Paradise Tropical Village
Apartment
Key West, FL, USA
0.7k from Higgs Beach center

Pool, Parking, Security/Safety, View, Sports/Activities, Spa, Barbecue/Outdoor Cooking

1 Bedroom2 Guests
New to Booking
$400
Average price / night
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Key West Private Pool Garden Villa - 2 Blocks from Beach
Key West Private Pool Garden Villa - 2 Blocks from Beach
House
Key West, FL, 33040, United States
0.4k from Higgs Beach center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
9.8

Exceptional

24 reviews

$1084
Average price / night
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The Southern Cross Tropical Village
The Southern Cross Tropical Village
House
Key West, FL, USA
0.7k from Higgs Beach center

Pool, Parking, Security/Safety, View, Sports/Activities, Spa, Barbecue/Outdoor Cooking

2 Bedrooms6 Guests
New to Booking
$607
Average price / night
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Newly renovated home close to the beach and all attractions
Newly renovated home close to the beach and all attractions
House
Key West, FL, 33040, United States
0.4k from Higgs Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$476
Average price / night
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Alexander Palms Court - No Hidden Resort Fees!
Alexander Palms Court - No Hidden Resort Fees!
House
Key West, FL, USA
0.7k from Higgs Beach center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay

12 Bedrooms35 Guests
8.6

Fabulous

894 reviews

$225
Average price / night
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Sunshine Escape- 3 bedroom 3 bath w/ parking for 2, private pool, balcony
Sunshine Escape- 3 bedroom 3 bath w/ parking for 2, private pool, balcony
House
Key West, FL, 33040, United States
0.4k from Higgs Beach center

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

3 Bedrooms6 Guests
New to Booking
$268
Average price / night
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Sunnyside Up
Sunnyside Up
Apartment
Key West, FL, USA
0.7k from Higgs Beach center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms9 Guests
9.0

Fabulous

2 reviews

$655
Average price / night
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Paradise on Von Phister, only a 5 min walk to the Beach!
Paradise on Von Phister, only a 5 min walk to the Beach!
House
Key West, FL, 33040, United States
0.4k from Higgs Beach center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$480
Average price / night
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Tropical Vibes
Tropical Vibes
House
Key West, FL, USA
0.8k from Higgs Beach center

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

4 Bedrooms8 Guests
New to Booking
$515
Average price / night
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GOLDEN HOUR ~ Upscale 2 BR/2Ba Home w/ Pool!
GOLDEN HOUR ~ Upscale 2 BR/2Ba Home w/ Pool!
House
Key West, FL, 33040, United States
0.4k from Higgs Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$470
Average price / night
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ALOHA - Large 1 level 4bd/4ba Monthly Rental
ALOHA - Large 1 level 4bd/4ba Monthly Rental
House
Key West, FL, 33040, United States
0.5k from Higgs Beach center

AC, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

4 Bedrooms10 Guests
New to Booking
$503
Average price / night
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Glimmer Glass oceanfront condo by Rent Key West Hideaways
Glimmer Glass oceanfront condo by Rent Key West Hideaways
Condo
Key West, FL, 33040, United States
0.5k from Higgs Beach center

AC, Balcony, Dryer, Elevator, Free Parking, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$842
Average price / night
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Serendipity South: Premium Key West Pool Oasis Near The Beach
Serendipity South: Premium Key West Pool Oasis Near The Beach
House
Key West, FL, 33040, United States
0.5k from Higgs Beach center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, No Smoking, Patio, Pool

3 Bedrooms6 Guests
8.0

Good

1 reviews

$323
Average price / night
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Beach Club #103 - Unique oceanfront living with breathtaking views
Beach Club #103 - Unique oceanfront living with breathtaking views
Condo
Key West, FL, 33040, United States
0.5k from Higgs Beach center

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

2 Bedrooms5 Guests
9.4

Superb

133 reviews

$670
Average price / night
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Beach Club #104 - Unique oceanfront living with breathtaking views
Beach Club #104 - Unique oceanfront living with breathtaking views
Condo
Key West, FL, 33040, United States
0.5k from Higgs Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.2

Superb

82 reviews

$612
Average price / night
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OCEANFRONT ECSTASY - KW Beach Club #304
OCEANFRONT ECSTASY - KW Beach Club #304
Condo
Key West, FL, 33040, United States
0.5k from Higgs Beach center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.6

Exceptional

79 reviews

$688
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 Higgs Beach.

Where to stay in Higgs Beach? Best neighborhoods & areas

Higgs Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in Higgs Beach. 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 Higgs Beach vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $225 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Higgs Beach 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 Higgs Beach welcome pets. Currently, 27 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 Higgs Beach often include additional outdoor features such as Pool, Laundry, and Balcony/Terrace. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Higgs Beach 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.