Vacation Rentals with Pool in Upper Sugarloaf Sound, FL: Compare 10+ Sites & Save

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  1. VBOR
  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Sugarloaf Key
  6.  Upper Sugarloaf Sound

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262 Best Vacation Rentals with Pool in Upper Sugarloaf Sound (Starting from $308)

Villa of the Setting Sun
Villa of the Setting Sun
House
Upper Sugarloaf Sound, Sugarloaf Key, Florida, USA
1.4k from Upper Sugarloaf Sound 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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**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
**BLUE HORIZON @ SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
House
Sugarloaf Key, FL, 33042, United States
1.5k from Upper Sugarloaf Sound center

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

4 Bedrooms8 Guests
New to Booking
$638
Average price / night
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Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
2.2k from Upper Sugarloaf Sound 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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Villa and Bungalow of Pelico Palms
Villa and Bungalow of Pelico Palms
Villa
Monroe County, FL, 33042, United States
1.7k from Upper Sugarloaf Sound center

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

6 Bedrooms14 Guests
New to Booking
$1751
Average price / night
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Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages
House
Summerland Key, FL, USA
2.5k from Upper Sugarloaf Sound 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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The Villa of Pelico Palms
The Villa of Pelico Palms
House
Monroe County, FL, 33042, United States
1.7k from Upper Sugarloaf Sound center

AC, Arcade, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms10 Guests
10.0

Exceptional

6 reviews

$1512
Average price / night
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Newly built home in Cudjoe Key
Newly built home in Cudjoe Key
House
Cudjoe Key, FL, USA
4.1k from Upper Sugarloaf Sound center

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

3 Bedrooms7 Guests
New to Booking
$583
Average price / night
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Private Pool Oasis — 3 King Suites | 30 Min to Key West
Private Pool Oasis — 3 King Suites | 30 Min to Key West
House
Monroe County, FL, 33042, United States
1.7k from Upper Sugarloaf Sound center

AC, Barbecue, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms7 Guests
7.6

Good

5 reviews

$945
Average price / night
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Bungalows Beach Key West - Azucar
Bungalows Beach Key West - Azucar
House
Key West, FL, USA
4.4k from Upper Sugarloaf Sound 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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Pelico Palms Estate.
Pelico Palms Estate.
House
Monroe County, FL, 33042, United States
1.7k from Upper Sugarloaf Sound center

AC, Arcade, Balcony, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area

9 Bedrooms20 Guests
9.8

Exceptional

7 reviews

$3053
Average price / night
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Luxury OceanView Friendly Villa Near Key West
Luxury OceanView Friendly Villa Near Key West
Villa
Upper Sugarloaf Sound, Sugarloaf Key, Florida, USA
4.5k from Upper Sugarloaf Sound center

Pool, Parking, Laundry, Hot Tub, Balcony/Terrace, Pet Friendly, Kitchen

4 Bedrooms10 Guests
1.0

Review score

1 reviews

$804
Average price / night
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Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Dining & Pet Friendly!
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Dining & Pet Friendly!
House
Sugarloaf Key, FL, 33042, United States
1.8k from Upper Sugarloaf Sound center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$383
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
4.6k from Upper Sugarloaf Sound 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 Paradise: 4 bedroom/5 bathroom, oceanfront with pool
Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool
House
Summerland Key, FL, 33042, United States
2.1k from Upper Sugarloaf Sound center

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

4 Bedrooms8 Guests
New to Booking
$1035
Average price / night
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Ocean View with Pool, 4 bedroom Vila Near Key West
Ocean View with Pool, 4 bedroom Vila Near Key West
Villa
Cudjoe Key, FL, USA
4.7k from Upper Sugarloaf Sound center

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

4 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$810
Average price / night
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$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
2.1k from Upper Sugarloaf Sound center

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

4 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$552
Average price / night
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Bungalows Beach Rental Key West - Lighthouse
Bungalows Beach Rental Key West - Lighthouse
House
Sugarloaf Shores, FL, USA
4.7k from Upper Sugarloaf Sound 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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Swimming Pool / Boat Dock / Close to Key West
Swimming Pool / Boat Dock / Close to Key West
House
Sugarloaf, FL, 33042, United States
2.2k from Upper Sugarloaf Sound center

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

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
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Bungalows Beach Key West - Hemingway
Bungalows Beach Key West - Hemingway
House
FL, USA
4.7k from Upper Sugarloaf Sound 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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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
2.2k from Upper Sugarloaf Sound 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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Unit 101
Unit 101
House
Cudjoe Key, FL, USA
5.2k from Upper Sugarloaf Sound center

Security/Safety, Pool, Hot Tub, Wellness Facilities, Air Conditioner, View, Balcony/Terrace

5 Bedrooms6 Guests
New to Booking
$405
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
2.3k from Upper Sugarloaf Sound center

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

2 Bedrooms6 Guests
New to Booking
$428
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
2.4k from Upper Sugarloaf Sound 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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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
2.4k from Upper Sugarloaf Sound center

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

4 Bedrooms10 Guests
9.8

Exceptional

14 reviews

$641
Average price / night
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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
2.5k from Upper Sugarloaf Sound center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$402
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
2.8k from Upper Sugarloaf Sound 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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Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront
Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront
House
Sugarloaf Key, FL, 33042, United States
2.8k from Upper Sugarloaf Sound 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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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 Upper Sugarloaf Sound.

Where to stay in Upper Sugarloaf Sound? Best neighborhoods & areas

Upper Sugarloaf Sound Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 262 verified vacation rentals with a pool in Upper Sugarloaf Sound. 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 Upper Sugarloaf Sound vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $308 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Upper Sugarloaf Sound 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 Upper Sugarloaf Sound welcome pets. Currently, 36 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 Upper Sugarloaf Sound often include additional outdoor features such as Pool, Balcony/Terrace, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Upper Sugarloaf Sound 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.