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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Higgs Beach

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485 Best Vacation Rentals with Private Pool in Higgs Beach (Starting from $245)

Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
House
Higgs Beach, Key West, Florida, USA
1.6k from Higgs Beach center

Pool, Private Pool, Kitchen, Parking, Internet, Air Conditioner, Child Friendly

1 Bedroom4 Guests
New to Booking
$348
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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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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**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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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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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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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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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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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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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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A Bella Capri in Key West by the Beach!
A Bella Capri in Key West by the Beach!
House
Key West, FL, 33040, United States
0.5k from Higgs Beach center

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

5 Bedrooms10 Guests
9.4

Superb

6 reviews

$612
Average price / night
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**LAYOVER in PARADISE @ CASA MARINA** New Home / Pool + LAST KEY SERVICES…
**LAYOVER in PARADISE @ CASA MARINA** New Home / Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.5k from Higgs Beach center

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

3 Bedrooms8 Guests
New to Booking
$505
Average price / night
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Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
House
Key West, FL, 33040, United States
0.5k from Higgs Beach center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Dryer, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$557
Average price / night
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SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w/ Pool!
SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w/ Pool!
House
Key West, FL, 33040, United States
0.6k from Higgs Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$636
Average price / night
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Starfish Oasis at Casa Marina, 2BR - Heated Pool - Hot Tub - 2 Parking - Pets OK
Starfish Oasis at Casa Marina, 2BR - Heated Pool - Hot Tub - 2 Parking - Pets OK
House
Key West, FL, 33040, United States
0.6k from Higgs Beach center

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

2 Bedrooms4 Guests
New to Booking
$358
Average price / night
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Tropical 3BR Casa Marina Retreat w/ Private Pool — Steps to Higgs Beach
Tropical 3BR Casa Marina Retreat w/ Private Pool — Steps to Higgs Beach
House
Key West, FL, 33040, United States
0.6k from Higgs Beach center

AC, Barbecue, Dryer, Kitchen, Microwave, No Smoking, Pool, TV, Washer

3 Bedrooms8 Guests
New to Booking
$251
Average price / night
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**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
House
Key West, FL, 33040, United States
0.6k from Higgs Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$483
Average price / night
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GARDEN OASIS ~ Great Casa Marina Location with True Island Elegance!
GARDEN OASIS ~ Great Casa Marina Location with True Island Elegance!
House
Key West, FL, 33040, United States
0.6k from Higgs Beach center

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

4 Bedrooms8 Guests
9.8

Exceptional

27 reviews

$511
Average price / night
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SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!
SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!
House
Key West, FL, 33040, United States
0.6k from Higgs Beach center

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

4 Bedrooms12 Guests
10.0

Exceptional

8 reviews

$903
Average price / night
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SOUL OF THE SEA ~ Charming 3 BR, 3 Ba Home w/ Pool and Parking!
SOUL OF THE SEA ~ Charming 3 BR, 3 Ba Home w/ Pool and Parking!
House
Key West, FL, 33040, United States
0.6k from Higgs Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$426
Average price / night
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~SANCTUARY ON SOUTH~ A pool, privacy and posh design abound!
~SANCTUARY ON SOUTH~ A pool, privacy and posh design abound!
House
Key West, FL, 33040, United States
0.6k from Higgs Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$648
Average price / night
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Escape to Key West @ ROYAL ESCAPE
Escape to Key West @ ROYAL ESCAPE
House
Key West, FL, 33040, United States
0.7k from Higgs Beach center

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

3 Bedrooms10 Guests
9.6

Exceptional

98 reviews

$1270
Average price / night
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Beautiful 3bd/2ba Monthly Rental - ROYAL HAVEN
Beautiful 3bd/2ba Monthly Rental - ROYAL HAVEN
House
Key West, FL, 33040, United States
0.7k from Higgs Beach center

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

3 Bedrooms6 Guests
New to Booking
$339
Average price / night
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INTO THE BLUE~GRAND OPENING RATES! Pristine 4 BR/3.5 BA Home w/Private Pool!
INTO THE BLUE~GRAND OPENING RATES! Pristine 4 BR/3.5 BA Home w/Private Pool!
House
Key West, FL, 33040, United States
0.7k from Higgs Beach center

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

4 Bedrooms8 Guests
New to Booking
$364
Average price / night
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THE GREEN COCONUT ~ Updated 3 BR, 2 Ba Home w/ Parking and Private Pool!
THE GREEN COCONUT ~ Updated 3 BR, 2 Ba Home w/ Parking and Private Pool!
House
Key West, FL, 33040, United States
0.7k from Higgs Beach center

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

3 Bedrooms6 Guests
New to Booking
$404
Average price / night
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POOLSIDE PARADISE ~ Charming 3 BR/2Ba Home w/ Pool!
POOLSIDE PARADISE ~ Charming 3 BR/2Ba Home w/ Pool!
House
Key West, FL, 33040, United States
0.7k from Higgs Beach center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

3 Bedrooms8 Guests
New to Booking
$407
Average price / night
Check Availability

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 Private Pool in Higgs Beach.

Where to stay in Higgs Beach? Best neighborhoods & areas

Higgs Beach Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 485 verified vacation rentals with a private pool in Higgs Beach. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Higgs Beach vary depending on the property size, location, and travel season. Rates typically start from around $245 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Higgs Beach also welcome pets. Currently, 30 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Higgs Beach often include additional features such as Pool, Private Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Higgs Beach include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.