Beach Home Rentals in Simonton Beach, FL: Compare 10+ Sites & Save

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1018 Beach Home Rentals in Simonton Beach (Starting from $225)

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
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Key West Beach Front Studio! The only private Ocean and Beach View stay!
Key West Beach Front Studio! The only private Ocean and Beach View stay!
Apartment
Key West, FL, 33040, United States
0.1k from Simonton Beach center

AC, Barbecue, Elevator, Internet, Kitchen, Microwave, No Smoking, Patio, Pool

1 Bedroom2 Guests
9.8

Exceptional

141 reviews

$684
Average price / night
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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
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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
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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
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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
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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 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
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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
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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
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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
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Chic 2 Bedroom Condo 300 Steps from Duval St
Chic 2 Bedroom Condo 300 Steps from Duval St
Apartment
Key West, FL, USA
0.6k from Simonton Beach center

Wheelchair Accessible, Ocean View, Pet Friendly, Parking, Air Conditioner, Smoking, View

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$276
Average price / night
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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
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Old Town Garden Villas
Old Town Garden Villas
House
Simonton Beach, Key West, Florida, USA
0.7k from Simonton Beach center

View, Internet, Pool, Air Conditioner, Ocean View, Child Friendly

2 Bedrooms8 Guests
9.5

Superb

19 reviews

$258
Average price / night
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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
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Elizabeth's Secret - Old Town Key West
Elizabeth's Secret - Old Town Key West
House
Key West, FL, USA
0.8k from Simonton Beach center

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

3 Bedrooms6 Guests
New to Booking
$1628
Average price / night
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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
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The Pirates Penthouse by Last Key Realty
The Pirates Penthouse by Last Key Realty
Apartment
Key West, FL, USA
1.0k from Simonton Beach center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
9.3

Superb

3 reviews

$964
Average price / night
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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
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Courtney's Place Historic Cottages & Inns
Courtney's Place Historic Cottages & Inns
House
Simonton Beach, Key West, Florida, USA
1.0k from Simonton Beach center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Romantic, Pet-friendly, Lodgings

18 Bedrooms72 Guests
8.8

Fabulous

1291 reviews

$738
Average price / night
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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
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New Orleans House - Gay Male Adult Guesthouse
New Orleans House - Gay Male Adult Guesthouse
House
Simonton Beach, Key West, Florida, USA
1.0k from Simonton Beach center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Hot tubs

13 Bedrooms28 Guests
8.8

Fabulous

193 reviews

$575
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
0.2k 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
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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
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Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Cottage
427 B Catherine St, Key West, FL, 33040, United States
0.2k from Simonton Beach center

AC, Dryer, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, Washer And Dryer

10.0

Exceptional

6 reviews

$916
Average price / night
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HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$328
Average price / night
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Garden of Roses | Private Hot Tub, Prime Key West Location!
Garden of Roses | Private Hot Tub, Prime Key West Location!
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

3 Bedrooms8 Guests
New to Booking
$257
Average price / night
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Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
Apartment
Key West, FL, 33040, United States
0.3k from Simonton Beach center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

1 Bedroom4 Guests
9.6

Exceptional

44 reviews

$448
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 Beach Rentals in Simonton Beach.

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Frequently Asked Questions

You can explore 1018 verified beach rentals in Simonton Beach. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Simonton Beach vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $225 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Simonton Beach offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Simonton Beach welcome pets. Currently, 38 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Simonton Beach often include amenities designed for coastal living, such as View, Ocean View, and Internet. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.