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

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  2. Vacation Rentals with Private Pool
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  4.  Florida
  5.  Sugarloaf Key

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71 Best Vacation Rentals with Private Pool in Sugarloaf Key (Starting from $308)

**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
1.2k from Sugarloaf Key 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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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
1.4k from Sugarloaf Key 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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Swimming Pool / Boat Dock / Close to Key West
Swimming Pool / Boat Dock / Close to Key West
House
Sugarloaf, FL, 33042, United States
1.8k from Sugarloaf Key center

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

4 Bedrooms8 Guests
New to Booking
$308
Average price / night
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$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
1.8k from Sugarloaf Key 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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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
1.9k from Sugarloaf Key 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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Sunset Views • Heated Pool • Fire Pit • Sleeps 6
Sunset Views • Heated Pool • Fire Pit • Sleeps 6
House
Sugarloaf Key, FL, 33042, United States
2.0k from Sugarloaf Key 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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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
2.1k from 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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Pelico Palms Estate.
Pelico Palms Estate.
House
Monroe County, FL, 33042, United States
2.1k from 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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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
2.2k from Sugarloaf Key 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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SUGARLOAF OASIS - heated pool & boat dock
SUGARLOAF OASIS - heated pool & boat dock
House
Sugarloaf Key, FL, 33042, United States
2.6k from Sugarloaf Key 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
2.6k from Sugarloaf Key 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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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
2.7k from Sugarloaf Key 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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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
4.2k from 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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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
4.3k from 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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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
4.4k from 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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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
4.5k from 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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Private Beach House w/Pool
Private Beach House w/Pool
House
Cudjoe Key, FL, 33042, United States
4.5k from 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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Private Secluded Ocean View & Pool Near Key West
Private Secluded Ocean View & Pool Near Key West
House
Summerland Key, FL, 33042, United States
4.7k from 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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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
4.7k from 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
4.7k from 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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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
4.8k from 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
4.8k from 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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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
4.8k from 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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Upscale Canal-Front Escape w/ Private Pool, Dock & Water Views
Upscale Canal-Front Escape w/ Private Pool, Dock & Water Views
House
Cudjoe Key, FL, 33042, United States
4.9k from Sugarloaf Key center

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

3 Bedrooms6 Guests
New to Booking
$341
Average price / night
Check Availability
Fisherman's Paradise
Fisherman's Paradise
House
Cudjoe Key, FL, 33042, United States
4.9k from Sugarloaf Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$884
Average price / night
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Villa Jekjak
Villa Jekjak
House
Summerland Key, FL, 33042, United States
4.9k from Sugarloaf Key center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$407
Average price / night
Check Availability
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
5.0k from Sugarloaf Key center

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

5 Bedrooms12 Guests
New to Booking
$703
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 Private Pool in Sugarloaf Key.

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Sugarloaf Key Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 71 verified vacation rentals with a private pool in Sugarloaf Key. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Sugarloaf Key vary depending on the property size, location, and travel season. Rates typically start from around $308 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Sugarloaf Key also welcome pets. Currently, 34 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Sugarloaf Key often include additional features such as Kitchen, Laundry, and Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Sugarloaf Key include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.