Vacation Rentals with Pool in Saddlebunch Keys, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Key West
  6.  Saddlebunch Keys

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40 Best Vacation Rentals with Pool in Saddlebunch Keys (Starting from $281)

Bungalows Beach Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
4.6k from Saddlebunch Keys center

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

2 Bedrooms4 Guests
New to Booking
$1395
Average price / night
Check Availability
Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount
Available Florida Keys pool home near Key West. 2025 Sum/Fall 30% off discount
House
Key West, FL, 33040, United States
2.5k from Saddlebunch Keys center

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

4 Bedrooms8 Guests
9.4

Superb

15 reviews

$346
Average price / night
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Bungalows Beach Key West - Hemingway
Bungalows Beach Key West - Hemingway
House
FL, USA
4.6k from Saddlebunch Keys 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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Key West Beach House with heated pool, tiki, and dock.♿︎
Key West Beach House with heated pool, tiki, and dock.♿︎
House
Key West, FL, 33040, United States
2.5k from Saddlebunch Keys center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms10 Guests
9.6

Exceptional

8 reviews

$646
Average price / night
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Bungalows Sugarloaf Beach Key West - Hammock House
Bungalows Sugarloaf Beach Key West - Hammock House
House
Sugarloaf Shores, FL, USA
4.7k from Saddlebunch Keys 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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Sunset Bay: Spacious 5BR Getaway, Dockage, Heated Pool, Dog OK, Stunning Views & Minutes to Key West
Sunset Bay: Spacious 5BR Getaway, Dockage, Heated Pool, Dog OK, Stunning Views & Minutes to Key West
House
Saddlebunch Key, FL, 33040, United States
2.6k from Saddlebunch Keys center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, Kitchen, Microwave

5 Bedrooms10 Guests
9.8

Exceptional

8 reviews

$419
Average price / night
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Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
4.9k from Saddlebunch Keys 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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Home in Blue water Key
Home in Blue water Key
House
Key West, FL, 33040, United States
2.6k from Saddlebunch Keys center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$562
Average price / night
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Dock and Balcony Serene Big Coppitt Key Escape
Dock and Balcony Serene Big Coppitt Key Escape
House
Key West, FL, USA
5.6k from Saddlebunch Keys center

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

3 Bedrooms6 Guests
New to Booking
$281
Average price / night
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Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!
Waterfront Pool Oasis: Tiki Hut, Kayaks & Family Fun!
House
Key West, FL, 33040, United States
2.8k from Saddlebunch Keys center

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

4 Bedrooms8 Guests
New to Booking
$331
Average price / night
Check Availability
Ritaville - Monthly Rental
Ritaville - Monthly Rental
House
Stock Island, FL, USA
5.8k from Saddlebunch Keys center

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

4 Bedrooms11 Guests
New to Booking
$641
Average price / night
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Luxurious Oceanfront 5BR Property with heated Pool & Waterfall
Luxurious Oceanfront 5BR Property with heated Pool & Waterfall
House
Key West, FL, 33040, United States
2.8k from Saddlebunch Keys center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms12 Guests
10.0

Exceptional

9 reviews

$851
Average price / night
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Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
6.5k from Saddlebunch Keys 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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Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!
Your own Private Resort! 50ft Dock on Canal w/ Pool, Tiki and RV Hookup!
House
Key West, FL, 33040, United States
2.8k from Saddlebunch Keys center

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

4 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$703
Average price / night
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Villa of the Setting Sun
Villa of the Setting Sun
House
Saddlebunch Keys, Key West, Florida, USA
9.5k from Saddlebunch Keys 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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Ocean 9 Villa, Amazing Waterfront, 15 mins away from Duval Street!
Ocean 9 Villa, Amazing Waterfront, 15 mins away from Duval Street!
House
Key West, FL, 33040, United States
3.3k from Saddlebunch Keys center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms12 Guests
New to Booking
$703
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
4.7k from Saddlebunch Keys 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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Blue Gem | Family-Friendly Waterfront  w/Pool, Tiki Bar/Dock (Monthly Stay)
Blue Gem | Family-Friendly Waterfront w/Pool, Tiki Bar/Dock (Monthly Stay)
House
Key West, FL, 33040, United States
5.2k from Saddlebunch Keys center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$329
Average price / night
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Beautiful 3 bedroom 2 bath pool house close to Key West
Beautiful 3 bedroom 2 bath pool house close to Key West
House
Big Coppitt Key, FL, 33040, United States
5.3k from Saddlebunch Keys center

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

3 Bedrooms6 Guests
New to Booking
$400
Average price / night
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Fisherman's Paradise on the Water
Fisherman's Paradise on the Water
House
Key West, FL, 33040, United States
5.3k from Saddlebunch Keys center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$369
Average price / night
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Custom Pool home with Dazzling Ocean Views of the crystal clear Florida Keys waters!
Custom Pool home with Dazzling Ocean Views of the crystal clear Florida Keys waters!
House
Big Coppitt Key, FL, 33040, United States
5.3k from Saddlebunch Keys center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Hot Tub, Internet

3 Bedrooms8 Guests
New to Booking
$608
Average price / night
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The Perfect Catch: Family Fun and Boater's Bliss in the Keys!
The Perfect Catch: Family Fun and Boater's Bliss in the Keys!
House
Lower Florida Keys, FL, 33042, United States
5.6k from Saddlebunch Keys center

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

4 Bedrooms10 Guests
New to Booking
$684
Average price / night
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**INFINITE HORIZONS @ BIG COPPITT** Waterfront Home & Pool + LAST KEY SERVICES…
**INFINITE HORIZONS @ BIG COPPITT** Waterfront Home & Pool + LAST KEY SERVICES…
House
Key West, FL, 33040, United States
5.6k from Saddlebunch Keys center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$757
Average price / night
Check Availability
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and Dog-Friendly Perks!
House
Sugarloaf, FL, 33042, United States
5.9k from Saddlebunch Keys center

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

4 Bedrooms10 Guests
9.8

Exceptional

14 reviews

$641
Average price / night
Check Availability
Lock in summer months. For up to date availability\n510-381-5000
Lock in summer months. For up to date availability\n510-381-5000
House
Sugarloaf, FL, 33042, United States
6.0k from Saddlebunch Keys center

AC, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$402
Average price / night
Check Availability
PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.
House
Summerland Key, FL, 33042, United States
6.0k from Saddlebunch Keys center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$384
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
6.3k from Saddlebunch Keys center

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

2 Bedrooms6 Guests
New to Booking
$428
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 with Pool in Saddlebunch Keys.

Where to stay in Saddlebunch Keys? Best neighborhoods & areas

Saddlebunch Keys Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 40 verified vacation rentals with a pool in Saddlebunch Keys. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Saddlebunch Keys vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $281 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Saddlebunch Keys offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Saddlebunch Keys welcome pets. Currently, 22 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Saddlebunch Keys often include additional outdoor features such as Pool, Balcony/Terrace, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Saddlebunch Keys offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.