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

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  4.  Florida
  5.  Key West
  6.  Smathers Beach

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604 Best Family Vacation Rentals 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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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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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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Oceanview at 1800 Atlantic, short walk to Smathers Beach wish Island Paradise
Oceanview at 1800 Atlantic, short walk to Smathers Beach wish Island Paradise
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

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

2 Bedrooms6 Guests
9.2

Superb

21 reviews

$528
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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 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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Penthouse Beach Ocean Views-  Live the Dream
Penthouse Beach Ocean Views- Live the Dream
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

2 Bedrooms6 Guests
9.8

Exceptional

257 reviews

$731
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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Beach Penthouse: Ocean Views from every room  Tropical Excellence
Beach Penthouse: Ocean Views from every room Tropical Excellence
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

2 Bedrooms6 Guests
9.8

Exceptional

227 reviews

$718
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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Panoramic Ocean: Beach from every window
Panoramic Ocean: Beach from every window
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

2 Bedrooms6 Guests
9.8

Exceptional

333 reviews

$751
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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🏝️3 Bdrm - Ocean View Every Room-Secluded -Quiet-OCEAN FRONT- 90 FT BALCONY
🏝️3 Bdrm - Ocean View Every Room-Secluded -Quiet-OCEAN FRONT- 90 FT BALCONY
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

17 reviews

$546
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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Sea Breeze at 1800 Atlantic
Sea Breeze at 1800 Atlantic
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
8.8

Fabulous

5 reviews

$276
Average price / night
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Tom's Oceanfront Penthouse
Tom's Oceanfront Penthouse
House
Key West, FL, USA
0.7k from Smathers Beach center

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

3 Bedrooms8 Guests
9.0

Fabulous

1 reviews

$907
Average price / night
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ATLANTIC HIDEAWAY- Key West
ATLANTIC HIDEAWAY- Key West
Condo
Key West, FL, 33040, United States
0.7k from Smathers Beach center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

2 Bedrooms6 Guests
9.6

Exceptional

73 reviews

$545
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
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Luxury High End, 2 Bikes,  Highspeed Wi-Fi, Work station,  Pool, Hot Tub, Gym
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Condo
Key West, FL, 33040, United States
0.8k from Smathers Beach center

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

1 Bedroom4 Guests
9.8

Exceptional

311 reviews

$490
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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Gorgeous beach bungalow just steps from the beach!
Gorgeous beach bungalow just steps from the beach!
House
Key West, FL, 33040, United States
1.0k from Smathers Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$223
Average price / night
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Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
House
Key West, FL, 33040, United States
1.1k from Smathers Beach center

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

3 Bedrooms8 Guests
6.8

Good

3 reviews

$699
Average price / night
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Private Paradise with Heated Waterfall Pool
Private Paradise with Heated Waterfall Pool
House
Key West, FL, 33040, United States
1.1k from Smathers Beach center

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

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$319
Average price / night
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SOUTHERNMOST SWIM AND SOCIAL CLUB
SOUTHERNMOST SWIM AND SOCIAL CLUB
House
Key West, FL, 33040, United States
1.2k from Smathers Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

5 reviews

$720
Average price / night
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Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
House
Key West, FL, 33040, United States
1.2k from Smathers Beach center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Dryer, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
10.0

Exceptional

3 reviews

$557
Average price / night
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BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
House
Key West, FL, 33040, United States
1.4k from Smathers Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$470
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 Family Vacation Rentals in Smathers Beach.

Where to stay in Smathers Beach? Best neighborhoods & areas

Smathers Beach Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 604 verified family-friendly vacation rentals in Smathers Beach. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Smathers Beach vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $198 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Smathers Beach offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Smathers Beach are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Smathers Beach often include amenities such as Child Friendly, Pool, and Wellness Facilities. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.