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

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  2. Vacation Rentals with Pool
  3.  USA

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

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292 Best Vacation Rentals with Pool in Upper Sugarloaf Key (Starting from $301)

Sugarloaf Key RV Resort & Cottages
Sugarloaf Key RV Resort & Cottages
House
Summerland Key, FL, USA
0.5k from Upper Sugarloaf Key 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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Villa and Bungalow of Pelico Palms
Villa and Bungalow of Pelico Palms
Villa
Monroe County, FL, 33042, United States
1.0k from Upper Sugarloaf Key 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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Villa of the Setting Sun
Villa of the Setting Sun
House
Upper Sugarloaf Key, Sugarloaf Key, Florida, USA
1.3k from Upper Sugarloaf Key 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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The Villa of Pelico Palms
The Villa of Pelico Palms
House
Monroe County, FL, 33042, United States
1.0k from Upper Sugarloaf Key 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
2.2k from Upper Sugarloaf Key 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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Pelico Palms Estate.
Pelico Palms Estate.
House
Monroe County, FL, 33042, United States
1.0k from Upper Sugarloaf Key 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 Key, Sugarloaf Key, Florida, USA
2.5k from Upper Sugarloaf Key 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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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
1.1k from Upper Sugarloaf Key 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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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
2.7k from Upper Sugarloaf Key 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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CUDJOE GARDENS SANCTUARY- 3 BED/ 2 BATH- POOL, SPA, RV HOOK UP, BRING YOUR BOAT
CUDJOE GARDENS SANCTUARY- 3 BED/ 2 BATH- POOL, SPA, RV HOOK UP, BRING YOUR BOAT
House
Cudjoe Key, FL, 33042, United States
1.7k from Upper Sugarloaf Key center

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

3 Bedrooms6 Guests
New to Booking
$486
Average price / night
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Unit 101
Unit 101
House
Cudjoe Key, FL, USA
3.3k from Upper Sugarloaf Key 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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3 Bedroom/2 Bath Canal Home w/ Private Pool and Large Concrete Dock- Cudjoe Key
3 Bedroom/2 Bath Canal Home w/ Private Pool and Large Concrete Dock- Cudjoe Key
House
Cudjoe Key, FL, 33042, United States
1.8k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
New to Booking
$424
Average price / night
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Waterfront home with a large dock, pool, and deck area. Can accommodate pets.
Waterfront home with a large dock, pool, and deck area. Can accommodate pets.
House
Summerland, FL, 33042, United States
1.8k from Upper Sugarloaf Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$412
Average price / night
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Sugarloaf Lodge
Sugarloaf Lodge
Cabin
Sugarloaf Shores, FL, USA
4.1k from Upper Sugarloaf Key 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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Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe
Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe
House
Summerland Key, FL, 33042, United States
2.0k from Upper Sugarloaf Key center

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

3 Bedrooms6 Guests
9.6

Exceptional

24 reviews

$336
Average price / night
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Key Lime Time
Key Lime Time
House
Cudjoe Key, FL, USA
4.5k from Upper Sugarloaf Key center

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

4 Bedrooms12 Guests
New to Booking
$363
Average price / night
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Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool
Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool
House
Cudjoe Key, FL, 33042, United States
2.2k from Upper Sugarloaf Key center

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

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$499
Average price / night
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Parrotfish Pointe
Parrotfish Pointe
House
Cudjoe Key, FL, USA
4.8k from Upper Sugarloaf Key center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

3 Bedrooms6 Guests
New to Booking
$301
Average price / night
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Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool
Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool
House
Cudjoe Key, FL, 33042, United States
2.3k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$393
Average price / night
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Dolphin Daydreams by Last Key Realty
Dolphin Daydreams by Last Key Realty
House
Cudjoe Key, FL, USA
5.3k from Upper Sugarloaf Key center

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

1 Bedroom4 Guests
New to Booking
$351
Average price / night
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Private Secluded Ocean View & Pool Near Key West
Private Secluded Ocean View & Pool Near Key West
House
Summerland Key, FL, 33042, United States
2.3k from Upper Sugarloaf Key center

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

4 Bedrooms10 Guests
8.0

Good

103 reviews

$750
Average price / night
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Private Beach House w/Pool
Private Beach House w/Pool
House
Cudjoe Key, FL, 33042, United States
2.3k from Upper Sugarloaf Key center

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

5 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$881
Average price / night
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Magnificent Ocean views, privacy abounds on this well appointed mini estate.
Magnificent Ocean views, privacy abounds on this well appointed mini estate.
House
Cudjoe Key, FL, 33042, United States
2.4k from Upper Sugarloaf Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$532
Average price / night
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Cozy 3-bedroom house with AC and WiFi in charming Cudjoe Key
Cozy 3-bedroom house with AC and WiFi in charming Cudjoe Key
House
Cudjoe Key, FL, 33042, United States
2.4k from Upper Sugarloaf Key center

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

3 Bedrooms6 Guests
New to Booking
$324
Average price / night
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Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapid Open Water Access!
Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapid Open Water Access!
House
Summerland Key, FL, 33042, United States
2.4k from Upper Sugarloaf Key center

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

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$516
Average price / night
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Breezy Palms: Exquisite Open Water Keys Paradise W/ Spectacular Views, Dockage, Pool & Dog-Friendly!
Breezy Palms: Exquisite Open Water Keys Paradise W/ Spectacular Views, Dockage, Pool & Dog-Friendly!
House
Cudjoe Key, FL, 33042, United States
2.4k from Upper Sugarloaf Key center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$463
Average price / night
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Gorgeous New 4/3 With Heated Pool/Spa And Large Deep Water Boat Dock
Gorgeous New 4/3 With Heated Pool/Spa And Large Deep Water Boat Dock
House
Cudjoe Key, FL, 33042, United States
2.5k from Upper Sugarloaf Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$349
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 Upper Sugarloaf Key.

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

Upper Sugarloaf Key Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 292 verified vacation rentals with a pool in Upper Sugarloaf Key. 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 Key vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $301 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Upper Sugarloaf Key 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 Key welcome pets. Currently, 31 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 Key often include additional outdoor features such as Pool, Laundry, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Upper Sugarloaf Key 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.