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

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Simonton Beach

Refine your search

Price per night

Amenity Filter

Rating

1469 Best Vacation Rentals with Pool in Simonton Beach (Starting from $136)

The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
0.1k from Simonton Beach center

Accommodations, Pools, Resorts, Parking, Spa, Pet-friendly, 4-star, Lodgings, Beach

130 Bedrooms42 Guests
7.6

Good

287 reviews

$418
Average price / night
Check Availability
Key West-Coconut Beach Resort - Avail 11/14/26 to 11/21/26
Key West-Coconut Beach Resort - Avail 11/14/26 to 11/21/26
Condo
Key West, FL, 33040, United States
0.1k from Simonton Beach center

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

1 Bedroom2 Guests
New to Booking
$253
Average price / night
Check Availability
Santa Maria Suites Resort
Santa Maria Suites Resort
Resort
Key West, FL, USA
0.1k from Simonton Beach center

Accommodations, Pools, Resorts, Parking, Romantic, Boutique, 4-star, Lodgings, Places to stay

35 Bedrooms20 Guests
9.3

Superb

674 reviews

$432
Average price / night
Check Availability
Poolside Paradise Tropical Village
Poolside Paradise Tropical Village
Apartment
Key West, FL, USA
0.2k from Simonton Beach center

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

1 Bedroom2 Guests
New to Booking
$400
Average price / night
Check Availability
Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
Tropical Dreaming by AvantStay | 4 BLKS to Beach! Private Pool!
House
Key West, FL, 33040, United States
0.1k from Simonton Beach center

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

2 Bedrooms6 Guests
9.6

Exceptional

104 reviews

$1350
Average price / night
Check Availability
The Southern Cross Tropical Village
The Southern Cross Tropical Village
House
Key West, FL, USA
0.2k from Simonton Beach center

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

2 Bedrooms6 Guests
New to Booking
$607
Average price / night
Check Availability
Coconut Beach Resort
Coconut Beach Resort
Resort
1500 Alberta St, Key West, FL, 33040, United States
0.1k from Simonton Beach center

AC, Barbecue, Business Services, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave

9.0

Fabulous

172 reviews

$650
Average price / night
Check Availability
Alexander Palms Court - No Hidden Resort Fees!
Alexander Palms Court - No Hidden Resort Fees!
House
Key West, FL, USA
0.3k from Simonton 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
Check Availability
Amelia Home by AvantStay | In Historic Old Town w/ Pool
Amelia Home by AvantStay | In Historic Old Town w/ Pool
House
Key West, FL, 33040, United States
0.1k from Simonton Beach center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, No Smoking

2 Bedrooms6 Guests
9.8

Exceptional

16 reviews

$1201
Average price / night
Check Availability
Queen of Louisa by Last Key Realty
Queen of Louisa by Last Key Realty
House
Key West, FL, USA
0.4k from Simonton Beach center

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

4 Bedrooms12 Guests
New to Booking
$856
Average price / night
Check Availability
Tropical Village: The Southern Cross - Quiet & gated. Pool/Porch/Pet friendly
Tropical Village: The Southern Cross - Quiet & gated. Pool/Porch/Pet friendly
Cottage
Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Barbecue, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms6 Guests
9.6

Exceptional

17 reviews

$742
Average price / night
Check Availability
Southernmost Hospitality VII by Last Key Realty
Southernmost Hospitality VII by Last Key Realty
House
Key West, FL, USA
0.4k from Simonton Beach center

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

7 Bedrooms16 Guests
New to Booking
$1607
Average price / night
Check Availability
Tropical Village: Tropical Hideaway - Quiet & gated. Pool/Patio
Tropical Village: Tropical Hideaway - Quiet & gated. Pool/Patio
House
Key West, FL, 33040, United States
0.2k from Simonton Beach center

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

2 Bedrooms4 Guests
8.8

Fabulous

11 reviews

$506
Average price / night
Check Availability
Southernmost Hospitality V by Last Key Realty
Southernmost Hospitality V by Last Key Realty
House
Key West, FL, USA
0.4k from Simonton Beach center

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

5 Bedrooms12 Guests
New to Booking
$1385
Average price / night
Check Availability
TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet & gated. Pool/Deck/Pet frien
TROPICAL COTTAGE by RENT KEY WEST VACATIONS - Quiet & gated. Pool/Deck/Pet frien
Cottage
Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Grill, Outdoor Space

2 Bedrooms5 Guests
9.8

Exceptional

26 reviews

$705
Average price / night
Check Availability
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton
Resort
Key West, FL, USA
0.4k from Simonton 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
Check Availability
Tropical Village: Toon Hall - Quiet & gated. Spacious! Pool/Decks/Pet friendly
Tropical Village: Toon Hall - Quiet & gated. Spacious! Pool/Decks/Pet friendly
House
Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Barbecue, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$971
Average price / night
Check Availability
H2O Suites- Adults Only
H2O Suites- Adults Only
Resort
Simonton Beach, Key West, Florida, USA
0.4k from Simonton Beach center

Luxury, Accommodations, Pools, Resorts, Parking, Romantic, 4-star, Lodgings, Places to stay

22 Bedrooms6 Guests
9.5

Superb

508 reviews

$1688
Average price / night
Check Availability
Tropical Village: Poolside Paradise by RENT KEY WEST VACATIONS
Tropical Village: Poolside Paradise by RENT KEY WEST VACATIONS
Apartment
Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Barbecue, Dryer, Kitchen, Laundry, Microwave, No Smoking, Outdoor Grill, Outdoor Space

1 Bedroom2 Guests
9.0

Fabulous

13 reviews

$388
Average price / night
Check Availability
Louisa's Garden
Louisa's Garden
Apartment
Key West, FL, USA
0.4k from Simonton Beach center

Pool, Balcony/Terrace, Restaurant, View, Security/Safety, Guest Services, Sports/Activities

1 Bedroom2 Guests
8.0

Good

2 reviews

$136
Average price / night
Check Availability
Tropical Village: 12BD/9BA Enclave for Large Groups. Gated. Pool/Hot Tub/Garden
Tropical Village: 12BD/9BA Enclave for Large Groups. Gated. Pool/Hot Tub/Garden
House
Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Balcony, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Grill

12 Bedrooms30 Guests
10.0

Exceptional

1 reviews

$3664
Average price / night
Check Availability
Point Break Suites
Point Break Suites
House
Simonton Beach, Key West, Florida, USA
0.4k from Simonton Beach center

Air Conditioner, Wheelchair Accessible, Parking, Pool, Laundry, Internet, Child Friendly

3 Bedrooms8 Guests
7.3

Good

3 reviews

$225
Average price / night
Check Availability
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
House
Key West, FL, 33040, United States
0.2k from Simonton Beach center

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

2 Bedrooms4 Guests
8.8

Fabulous

15 reviews

$663
Average price / night
Check Availability
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking
Condo
Key West, FL, 33040, United States
0.2k from Simonton Beach center

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

2 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$786
Average price / night
Check Availability
Kona Kai Oasis
Kona Kai Oasis
House
630 South Street, Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Barbecue, Free Parking, Internet, Outdoor Space, Pool, TV

8.2

Very Good

620 reviews

$370
Average price / night
Check Availability
**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
0.2k from Simonton 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
Check Availability
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps to Beach & Free Parking
House
Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Free Parking, Heater, Internet

5 Bedrooms12 Guests
10.0

Exceptional

149 reviews

$2141
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 Pool in Simonton Beach.

Where to stay in Simonton Beach? Best neighborhoods & areas

Simonton Beach Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1469 verified vacation rentals with a pool in Simonton 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 Simonton Beach vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $136 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Simonton 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 Simonton Beach welcome pets. Currently, 48 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 Simonton Beach often include additional outdoor features such as Pool, Internet, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Simonton 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.