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

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  5.  Key West
  6.  Smathers Beach

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1736 Best Vacation Rentals in Smathers Beach (Starting from $192)

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
Check Availability
Dune Wind South by AvantStay | Gated Community | Close to Beach
Dune Wind South by AvantStay | Gated Community | Close to Beach
House
Key West, FL, 33040, United States
0.4k from Smathers Beach center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, No Smoking, Patio, Pool

2 Bedrooms4 Guests
New to Booking
$205
Average price / night
Check Availability
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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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, 33040, United States
0.4k from Smathers Beach center

AC, Balcony, Dryer, Extra Bed, Hot Tub, Internet, Kitchen, Laundry, No Smoking

2 Bedrooms6 Guests
9.2

Superb

54 reviews

$814
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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Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!
Atlantic Paradise by AvantStay | Great Location w/ & Shared Pool and hot tub!
House
Key West, FL, 33040, United States
0.6k from Smathers Beach center

AC, Balcony, Dryer, Extra Bed, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
9.6

Exceptional

90 reviews

$777
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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 4-bedroom New Construction house with private pool in Key West
4-bedroom New Construction house with private pool in Key West
House
Key West, FL, 33040, United States
0.7k from Smathers Beach center

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

4 Bedrooms8 Guests
New to Booking
$778
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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💲 HUGE DISCOUNT for 28 day OCEAN FRONT! 90 FT BALCONY💰
💲 HUGE DISCOUNT for 28 day OCEAN FRONT! 90 FT BALCONY💰
Apartment
Key West, FL, 33040, United States
0.7k from Smathers Beach center

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

3 Bedrooms6 Guests
9.2

Superb

16 reviews

$633
Average price / night
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Luxury Island Resort Living at 1800 Atlantic, Pool, Beach, Tennis,in Key West
Luxury Island Resort Living at 1800 Atlantic, Pool, Beach, Tennis,in Key West
Apartment
Key West, FL, 33040, United States
0.8k from Smathers Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$227
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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Monthly Rentals Only - Key West Cottage Du Soleil
Monthly Rentals Only - Key West Cottage Du Soleil
Cottage
Key West, FL, 33040, United States
0.8k from Smathers Beach center

AC, Dryer, Laundry, Washer

2 Bedrooms4 Guests
New to Booking
$192
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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Tranquil tropical 3-bedroom house with AC in vibrant Key West.
Tranquil tropical 3-bedroom house with AC in vibrant Key West.
House
Key West, FL, 33040, United States
0.8k from Smathers Beach center

AC, Dryer, Heater, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$956
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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**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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NEW Atlantic Escape - Beach & Pool
NEW Atlantic Escape - Beach & Pool
Apartment
Key West, FL, USA
0.7k from Smathers Beach center

Apartments, Accommodations, Pools, Parking, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$205
Average price / night
Check Availability
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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Suite Sanctuary by Last Key Realty
Suite Sanctuary by Last Key Realty
Apartment
Key West, FL, USA
0.7k from Smathers Beach center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1003
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
Check Availability
CASA DE CANAL ~ Beautiful Renovated 3 BR, 2 Bath Canal Front Home w/Dockage!
CASA DE CANAL ~ Beautiful Renovated 3 BR, 2 Bath Canal Front Home w/Dockage!
House
Key West, FL, 33040, United States
0.9k from Smathers Beach center

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

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$208
Average price / night
Check Availability
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
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 in Smathers Beach.

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Frequently Asked Questions

You can explore 1736 verified vacation rentals in Smathers Beach. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Smathers Beach vary depending on the season, property size, and location. Rates typically start from around $192 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Smathers Beach include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Smathers Beach welcome pets. Currently, 29 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Smathers Beach often include amenities such as Wellness Facilities, Internet, and Pool. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.