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

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Smathers Beach

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485 Best Vacation Rentals with Private Pool in Smathers Beach (Starting from $143)

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
Smathers Beach, Key West, Florida, USA
2.8k from Smathers 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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Seaside Condo, DECEMBER SPECIAL
Seaside Condo, DECEMBER SPECIAL
Condo
Key West, FL, 33040, United States
0.1k from Smathers Beach center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Internet

1 Bedroom2 Guests
9.4

Superb

11 reviews

$216
Average price / night
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Spacious Ocean Front Resort - 3 Bedroom Condo
Spacious Ocean Front Resort - 3 Bedroom Condo
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub, Internet

3 Bedrooms8 Guests
9.2

Superb

189 reviews

$909
Average price / night
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Tom's Spectacular OceanFront 3 Bdrm  Endless Atlantic view, Key West Amazing
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Hot Tub, Internet

3 Bedrooms8 Guests
9.8

Exceptional

139 reviews

$940
Average price / night
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Luxury High End, 2 Bikes,  Highspeed Wi-Fi, Work station,  Pool, Hot Tub, Gym
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Condo
Key West, FL, 33040, United States
0.8k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
9.8

Exceptional

311 reviews

$490
Average price / night
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**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
**BELLE OF THE BEACH @ CASA EAST** Beach House + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.8k from Smathers Beach center

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

8 Bedrooms16 Guests
10.0

Exceptional

65 reviews

$2057
Average price / night
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Flagler's Oasis by AvantStay | Private Pool in Key West | Month Long Stays Only
Flagler's Oasis by AvantStay | Private Pool in Key West | Month Long Stays Only
House
Key West, FL, 33040, United States
0.8k from Smathers Beach center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
8.8

Fabulous

3 reviews

$279
Average price / night
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**BEAUTY OF THE BEACH** Monthly Beach House Rental + LAST KEY SERVICES…
**BEAUTY OF THE BEACH** Monthly Beach House Rental + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
0.8k from Smathers Beach center

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

6 Bedrooms12 Guests
New to Booking
$594
Average price / night
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BAREFOOT BUNGALOW~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!
BAREFOOT BUNGALOW~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!
House
Key West, FL, 33040, United States
0.9k from Smathers Beach center

AC, Barbecue, Dryer, Extra Bed, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.6

Exceptional

15 reviews

$302
Average price / night
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Waterfront Key West Home with Pool-Hot Tub on Riveria canal! 28 NIGHT MIN STAY.
Waterfront Key West Home with Pool-Hot Tub on Riveria canal! 28 NIGHT MIN STAY.
House
Key West, FL, 33040, United States
0.9k from Smathers Beach center

AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
9.4

Superb

9 reviews

$524
Average price / night
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Tranquil Retreat by the Beach-4 bedroom 3 bath home w/private pool, parking
Tranquil Retreat by the Beach-4 bedroom 3 bath home w/private pool, parking
House
Key West, FL, 33040, United States
0.9k from Smathers Beach center

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

4 Bedrooms8 Guests
8.0

Good

1 reviews

$289
Average price / night
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Double Lot Private Villa and Pool with Direct Boat Entry to Atlantic and Gulf.
Double Lot Private Villa and Pool with Direct Boat Entry to Atlantic and Gulf.
House
Key West, FL, 33040, United States
1.0k from Smathers Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Laundry, Pool, TV

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$578
Average price / night
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BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/ Pool!
BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/ Pool!
House
Key West, FL, 33040, United States
1.0k from Smathers Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$490
Average price / night
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Gorgeous beach bungalow just steps from the beach!
Gorgeous beach bungalow just steps from the beach!
House
Key West, FL, 33040, United States
1.0k from Smathers Beach center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$223
Average price / night
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OASIS SOUTH~Stunning 5 BR/3 Ba w/ Pool!
OASIS SOUTH~Stunning 5 BR/3 Ba w/ Pool!
House
Key West, FL, 33040, United States
1.0k from Smathers Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

5 Bedrooms14 Guests
9.8

Exceptional

7 reviews

$449
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
1.1k from Smathers 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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Private Paradise with Heated Waterfall Pool
Private Paradise with Heated Waterfall Pool
House
Key West, FL, 33040, United States
1.1k from Smathers Beach center

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

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$319
Average price / night
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**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
1.1k from Smathers Beach center

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

4 Bedrooms11 Guests
New to Booking
$676
Average price / night
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**THE ENCHANTED ROSE @ BEACHSIDE** Gorgeous Home & Pool + LAST KEY SERVICES…
**THE ENCHANTED ROSE @ BEACHSIDE** Gorgeous Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
1.1k from Smathers Beach center

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

3 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$466
Average price / night
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FLAMINGO ROSE ~ Midtown 3 Bedroom, 2 Bathroom Home w/ Pool & Parking!
FLAMINGO ROSE ~ Midtown 3 Bedroom, 2 Bathroom Home w/ Pool & Parking!
House
Key West, FL, 33040, United States
1.1k from Smathers Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$379
Average price / night
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Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!
Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!
House
Key West, FL, 33040, United States
1.1k from Smathers Beach center

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

3 Bedrooms6 Guests
New to Booking
$260
Average price / night
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POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
House
Key West, FL, 33040, United States
1.1k from Smathers Beach center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$577
Average price / night
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**73 PALMS @ MIDTOWN** Renovated Home & Pool + LAST KEY SERVICES…
**73 PALMS @ MIDTOWN** Renovated Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
1.2k from Smathers Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$379
Average price / night
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Island Time Escape - Charming Family Retreat
Island Time Escape - Charming Family Retreat
House
Key West, FL, 33040, United States
1.2k from Smathers Beach center

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

3 Bedrooms6 Guests
New to Booking
$376
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
1.2k from Smathers 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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**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach
**LARGE PRIVATE HEATED POOL and PATIO**1/3 Mile from Beach
House
Key West, FL, 33040, United States
1.2k from Smathers Beach center

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

2 Bedrooms8 Guests
10.0

Exceptional

19 reviews

$143
Average price / night
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SOUTHERNMOST SWIM AND SOCIAL CLUB
SOUTHERNMOST SWIM AND SOCIAL CLUB
House
Key West, FL, 33040, United States
1.2k from Smathers Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$720
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 Private Pool in Smathers Beach.

Where to stay in Smathers Beach? Best neighborhoods & areas

Smathers Beach Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 485 verified vacation rentals with a private pool in Smathers 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 Smathers Beach vary depending on the property size, location, and travel season. Rates typically start from around $143 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 Smathers 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 Smathers 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 Smathers 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.