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

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  2. Oceanfront Rentals
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  4.  Florida
  5.  Key West
  6.  Simonton Beach

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1053 Best Oceanfront 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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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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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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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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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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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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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 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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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: 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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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: 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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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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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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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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Heron Hideaway
Heron Hideaway
Apartment
Key West, FL, USA
1.1k from Simonton Beach center

Apartments, Cheap, Accommodations, Pools, Parking, Lodgings, Hot tubs, Places to stay, Family

1 Bedroom4 Guests
9.3

Superb

6 reviews

$384
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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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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Sea Esta Suite | Located On Iconic Duval w/ Pool
Sea Esta Suite | Located On Iconic Duval w/ Pool
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

2 Bedrooms6 Guests
9.8

Exceptional

41 reviews

$1002
Average price / night
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Royal Palm of Casa Marina
Royal Palm of Casa Marina
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

4 Bedrooms8 Guests
New to Booking
$429
Average price / night
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4-bedroom resort style home in awesome Key West with large pool and private deck
4-bedroom resort style home in awesome Key West with large pool and private deck
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1414
Average price / night
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Valhalla - in Old Town Key West
Valhalla - in Old Town Key West
House
Key West, FL, 33040, United States
0.3k from Simonton Beach center

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

2 Bedrooms4 Guests
New to Booking
$767
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 Oceanfront Rentals in Simonton Beach.

Where to stay in Simonton Beach? Best neighborhoods & areas

Simonton Beach Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1053 verified oceanfront rentals in Simonton Beach. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Simonton Beach vary depending on the property size, exact beachfront location, and season. Rates typically start from around $225 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Simonton Beach offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Simonton Beach welcome pets. Currently, 42 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Simonton Beach often include features designed for a comfortable coastal stay, such as View, Ocean View, and Oceanfront. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.