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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Smathers Beach

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1469 Best Vacation Rentals with Pool in Smathers Beach (Starting from $198)

Dune Wind South by AvantStay Communal Pool Hot Tub Gated Community Close to Smathers Beach Month Long Stays Only
Dune Wind South by AvantStay Communal Pool Hot Tub Gated Community Close to Smathers Beach Month Long Stays Only
House
Key West, FL, USA
0.5k from Smathers Beach center

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

2 Bedrooms4 Guests
New to Booking
$270
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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The Breeze
The Breeze
House
FL, USA
0.5k from Smathers Beach center

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

3 Bedrooms6 Guests
7.0

Good

2 reviews

$413
Average price / night
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Blue Escape-Beach Front, Ocean Views, Pool, AC, Kitchen, Patio
Blue Escape-Beach Front, Ocean Views, Pool, AC, Kitchen, Patio
Condo
Naval Air Station Key West, FL, 33040, United States
0.3k from Smathers Beach center

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

2 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$425
Average price / night
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La Brisa 108N
La Brisa 108N
Apartment
Smathers Beach, Key West, Florida, USA
0.5k from Smathers Beach center

Sports/Activities, Security/Safety, Pool, Barbecue/Outdoor Cooking, Hot Tub, Accessibility, Laundry

3 Bedrooms8 Guests
New to Booking
$198
Average price / night
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Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
Condo
Key West, FL, 33040, United States
0.4k from Smathers Beach center

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

2 Bedrooms4 Guests
9.4

Superb

134 reviews

$497
Average price / night
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La Brisa Unit 105 North Building
La Brisa Unit 105 North Building
House
Key West, FL, USA
0.5k from Smathers Beach center

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

2 Bedrooms6 Guests
8.3

Very Good

3 reviews

$796
Average price / night
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Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)
Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)
Condo
Key West, FL, 33040, United States
0.4k from Smathers Beach center

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

2 Bedrooms4 Guests
9.4

Superb

111 reviews

$478
Average price / night
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Color of the Keys
Color of the Keys
Apartment
Key West, FL, USA
0.5k from Smathers Beach center

Apartments, Accommodations, Pools, Pet-friendly, Lodgings, Hot tubs, Places to stay, Accessible hotels

2 Bedrooms6 Guests
New to Booking
$388
Average price / night
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Ocean views and beach breezes at La Brisa's #303 West
Ocean views and beach breezes at La Brisa's #303 West
Condo
Key West, FL, 33040, United States
0.4k from Smathers Beach center

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

2 Bedrooms4 Guests
8.4

Very Good

6 reviews

$200
Average price / night
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Brisa Del Mar by AvantStay Communal Pool Gated Community Ocean Front
Brisa Del Mar by AvantStay Communal Pool Gated Community Ocean Front
House
Key West, FL, USA
0.5k from Smathers Beach center

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

2 Bedrooms6 Guests
7.8

Good

5 reviews

$575
Average price / night
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 Steps To The Beach And The Sunrise
Steps To The Beach And The Sunrise
Condo
Key West, FL, 33040, United States
0.5k from Smathers Beach center

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

2 Bedrooms6 Guests
9.4

Superb

115 reviews

$242
Average price / night
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Oceanfront Oasis
Oceanfront Oasis
House
Key West, FL, USA
0.6k from Smathers Beach center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$620
Average price / night
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Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
Beach House- Ocean & Beach View-Upgraded-Over 146 Five Star Reviews
Condo
Key West, FL, 33040, United States
0.5k from Smathers Beach center

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

1 Bedroom2 Guests
9.8

Exceptional

163 reviews

$343
Average price / night
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Riviera Americana by Last Key Realty
Riviera Americana by Last Key Realty
House
Key West, FL, USA
0.6k from Smathers Beach center

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

3 Bedrooms8 Guests
New to Booking
$1257
Average price / night
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GATED OCEANFRONT CONDO AT SMATHER'S BEACH
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Condo
Key West, FL, 33040, United States
0.5k from Smathers Beach center

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

2 Bedrooms6 Guests
9.2

Superb

143 reviews

$427
Average price / night
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Tom's Chicken Coop Key West
Tom's Chicken Coop Key West
House
Key West, FL, USA
0.7k from Smathers Beach center

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

2 Bedrooms6 Guests
8.9

Fabulous

6 reviews

$642
Average price / night
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Your Condo by the Beach with Ocean View
Your Condo by the Beach with Ocean View
Condo
Key West, FL, 33040, United States
0.5k from Smathers Beach center

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

1 Bedroom2 Guests
10.0

Exceptional

164 reviews

$373
Average price / night
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Atlantic Sunrise Penthouse
Atlantic Sunrise Penthouse
House
Key West, FL, USA
0.7k from Smathers Beach center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$878
Average price / night
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By the Beautiful Sea - Key West Beach Front Condo - w Pool Access
By the Beautiful Sea - Key West Beach Front Condo - w Pool Access
Condo
Key West, FL, 33040, United States
0.5k from Smathers Beach center

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

3 Bedrooms6 Guests
9.2

Superb

75 reviews

$764
Average price / night
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La Brisa - Ocean Views Across from Smathers Beach
La Brisa - Ocean Views Across from Smathers Beach
Condo
Key West, FL, 33040, United States
0.5k from Smathers Beach center

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

2 Bedrooms6 Guests
10.0

Exceptional

142 reviews

$508
Average price / night
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The Crown Jewel of La Brisa 2 bdrm Monthly Spectacular ocean views.
The Crown Jewel of La Brisa 2 bdrm Monthly Spectacular ocean views.
Condo
Key West, FL, 33040, United States
0.5k from Smathers Beach center

Balcony, Dryer, Elevator, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
New to Booking
$201
Average price / night
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Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today
Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today
Condo
Key West, FL, 33040, United States
0.6k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.8

Exceptional

16 reviews

$464
Average price / night
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Direct Ocean View from Your Condo-No Contact Check-In
Direct Ocean View from Your Condo-No Contact Check-In
Condo
Key West, FL, 33040, United States
0.6k from Smathers Beach center

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

2 Bedrooms6 Guests
9.4

Superb

170 reviews

$358
Average price / night
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~VISTA FRESCO~ Oceanside condominiums with resort-style amenities
~VISTA FRESCO~ Oceanside condominiums with resort-style amenities
Condo
Key West, FL, 33040, United States
0.6k from Smathers Beach center

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

2 Bedrooms6 Guests
9.6

Exceptional

135 reviews

$509
Average price / night
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IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
Condo
Key West, FL, 33040, United States
0.6k from Smathers Beach center

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

2 Bedrooms6 Guests
9.4

Superb

190 reviews

$579
Average price / night
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Key West Beachfront Luxury 2/2 Condo A212
Key West Beachfront Luxury 2/2 Condo A212
Condo
Key West, FL, 33040, United States
0.6k from Smathers Beach center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking

2 Bedrooms6 Guests
10.0

Exceptional

166 reviews

$638
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 Smathers Beach.

Where to stay in Smathers Beach? Best neighborhoods & areas

Smathers Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in Smathers 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 Smathers Beach vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $198 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Smathers 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 Smathers Beach welcome pets. Currently, 2 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 Smathers Beach often include additional outdoor features such as Pool, Accessibility, and Sports/Activities. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Smathers 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.