Short-Term Rentals in Florida Keys Beaches, FL: Compare 10+ Sites & Save

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382 Best Short-Term Rentals in Florida Keys Beaches (Starting from $241)

Bungalows Sugarloaf Beach Key West - Hammock House
Bungalows Sugarloaf Beach Key West - Hammock House
House
Sugarloaf Shores, FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1695
Average price / night
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Beach Getaway in the Florida Keys
Beach Getaway in the Florida Keys
House
SUGARLOAF KEY, FL, 33042, United States
0.9k from Florida Keys Beaches center

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

2 Bedrooms8 Guests
8.4

Very Good

7 reviews

$1225
Average price / night
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Bungalows Beach Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

2 Bedrooms4 Guests
New to Booking
$1395
Average price / night
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Florida Keys Beach Getaway
Florida Keys Beach Getaway
House
Sugarloaf Key, FL, 33042, United States
0.9k from Florida Keys Beaches center

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

5 Bedrooms12 Guests
9.8

Exceptional

28 reviews

$1818
Average price / night
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Palms Resort Main House - Key West
Palms Resort Main House - Key West
House
Sugarloaf Shores, FL, USA
0.9k from Florida Keys Beaches center

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

1 Bedroom12 Guests
New to Booking
$1248
Average price / night
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Private and Exclusive Beach Getaway
Private and Exclusive Beach Getaway
House
Sugarloaf Key, FL, 33042, United States
0.9k from Florida Keys Beaches center

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

3 Bedrooms8 Guests
8.0

Good

2 reviews

$1969
Average price / night
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Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
0.9k from Florida Keys Beaches center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Places to stay

1 Bedroom8 Guests
New to Booking
$1198
Average price / night
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Bungalows Beach Key West - Hemingway
Bungalows Beach Key West - Hemingway
House
FL, USA
0.9k from Florida Keys Beaches center

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

2 Bedrooms6 Guests
New to Booking
$1104
Average price / night
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The Hemingway - Beach Houses Key West
The Hemingway - Beach Houses Key West
House
Upper Sugarloaf Key, FL, 33042, United States
1.0k from Florida Keys Beaches center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
9.6

Exceptional

8 reviews

$1291
Average price / night
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Coral Queen Palm
Coral Queen Palm
House
Key West, FL, USA
4.6k from Florida Keys Beaches center

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

3 Bedrooms6 Guests
New to Booking
$330
Average price / night
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The Lighthouse - Beach Houses Key West
The Lighthouse - Beach Houses Key West
House
Upper Sugarloaf Key, FL, 33042, United States
1.0k from Florida Keys Beaches center

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

2 Bedrooms4 Guests
9.6

Exceptional

11 reviews

$1893
Average price / night
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Waterfront Key West Oasis with Float Dock!
Waterfront Key West Oasis with Float Dock!
House
Key West, FL, USA
4.7k from Florida Keys Beaches center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$241
Average price / night
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Private and Exclusive Florida Keys Getaway
Private and Exclusive Florida Keys Getaway
House
Upper Sugarloaf Key, FL, 33042, United States
1.0k from Florida Keys Beaches center

AC, Balcony, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet

2 Bedrooms4 Guests
10.0

Exceptional

14 reviews

$1734
Average price / night
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Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
4.8k from Florida Keys Beaches center

Accommodations, Pools, Parking, Lodges, Cabins, Lodgings, Places to stay, Accessible hotels

13 Bedrooms10 Guests
7.4

Good

552 reviews

$313
Average price / night
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Beach Front - Cassie`s Paradise Key West
Beach Front - Cassie`s Paradise Key West
House
Key West, FL, 33040, United States
1.1k from Florida Keys Beaches center

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

4 Bedrooms8 Guests
New to Booking
$5664
Average price / night
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Villa of the Setting Sun
Villa of the Setting Sun
House
Florida Keys Beaches, Florida, USA
6.4k from Florida Keys Beaches center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

4 Bedrooms8 Guests
8.0

Good

1 reviews

$2804
Average price / night
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SUGARLOAF OASIS - heated pool & boat dock
SUGARLOAF OASIS - heated pool & boat dock
House
Sugarloaf Key, FL, 33042, United States
2.4k from Florida Keys Beaches center

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

1 Bedroom8 Guests
New to Booking
$562
Average price / night
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Pelico Paradise
Pelico Paradise
House
Florida Keys Beaches, Florida, USA
6.5k from Florida Keys Beaches center

Parking, Pet Friendly, Air Conditioner, Internet, Child Friendly

5 Bedrooms10 Guests
9.6

Exceptional

2 reviews

$304
Average price / night
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Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront
Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront
House
Sugarloaf Key, FL, 33042, United States
2.4k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms10 Guests
9.8

Exceptional

56 reviews

$610
Average price / night
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Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages
House
Summerland Key, FL, USA
6.7k from Florida Keys Beaches center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

20 Bedrooms12 Guests
9.0

Fabulous

314 reviews

$458
Average price / night
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Tropical paradise on canal in Lower Keys-pool, tiki, firepit, dock, dog friendly
Tropical paradise on canal in Lower Keys-pool, tiki, firepit, dock, dog friendly
House
Summerland Key, FL, 33042, United States
2.6k from Florida Keys Beaches center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$332
Average price / night
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Sunset Views • Heated Pool • Fire Pit • Sleeps 6
Sunset Views • Heated Pool • Fire Pit • Sleeps 6
House
Sugarloaf Key, FL, 33042, United States
2.7k from Florida Keys Beaches center

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

2 Bedrooms6 Guests
New to Booking
$428
Average price / night
Check Availability
 Canal Front 3-bedroom house in Sugarloaf Key
Canal Front 3-bedroom house in Sugarloaf Key
House
Summerland Key, FL, 33042, United States
2.9k from Florida Keys Beaches center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$343
Average price / night
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Serene 3-bedroom oceanfront house and dock in Sugarloaf Key
Serene 3-bedroom oceanfront house and dock in Sugarloaf Key
House
Summerland Key, FL, 33042, United States
2.9k from Florida Keys Beaches center

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

3 Bedrooms8 Guests
New to Booking
$308
Average price / night
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Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool
Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool
House
Summerland Key, FL, 33042, United States
3.0k from Florida Keys Beaches center

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

4 Bedrooms8 Guests
New to Booking
$1035
Average price / night
Check Availability
Swimming Pool / Boat Dock / Close to Key West
Swimming Pool / Boat Dock / Close to Key West
House
Sugarloaf, FL, 33042, United States
3.0k from Florida Keys Beaches center

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

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
Check Availability
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
House
Sugarloaf Key, FL, 33042, United States
3.0k from Florida Keys Beaches center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$552
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 Short-Term Rentals in Florida Keys Beaches.

Where to stay in Florida Keys Beaches? Best neighborhoods & areas

Florida Keys Beaches Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 382 verified short-term rentals in Florida Keys Beaches, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Florida Keys Beaches vary depending on location, property size, and travel dates. Rates typically start from around $241 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Florida Keys Beaches include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Florida Keys Beaches, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Florida Keys Beaches often include amenities such as Balcony/Terrace, View, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Florida Keys Beaches are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.