Vacation Rentals with Private Pool in Cutthroat Harbor Estates, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Cudjoe Key
  6.  Cutthroat Harbor Estates

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112 Best Vacation Rentals with Private Pool in Cutthroat Harbor Estates (Starting from $107)

Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!
House
Summerland Key, FL, 33042, United States
0.3k from Cutthroat Harbor Estates center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$773
Average price / night
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Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.
Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$337
Average price / night
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**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
**CAREFREE ON CUDJOE @ THE BAY** Waterfront Home & Pool + LAST KEY SERVICES…
House
Cudjoe Key, FL, 33042, United States
0.4k from Cutthroat Harbor Estates center

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

3 Bedrooms9 Guests
8.8

Fabulous

3 reviews

$483
Average price / night
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Night jasmine oceanfront vacation house
Night jasmine oceanfront vacation house
House
Cudjoe Key, FL, 33042, United States
0.5k from Cutthroat Harbor Estates center

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

4 Bedrooms10 Guests
10.0

Exceptional

27 reviews

$426
Average price / night
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The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
House
Summerland Key, FL, 33042, United States
0.6k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$339
Average price / night
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Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!
Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!
House
Summerland Key, FL, 33042, United States
0.6k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$223
Average price / night
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2 Bedroom Canal Home in Cudjoe Key, FL w/ Private Pool & Extra Loft Space
2 Bedroom Canal Home in Cudjoe Key, FL w/ Private Pool & Extra Loft Space
House
Cudjoe Key, FL, 33042, United States
0.7k from Cutthroat Harbor Estates center

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

2 Bedrooms6 Guests
New to Booking
$368
Average price / night
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Keys-y Livin only 20 minutes from Key West in the Florida Keys
Keys-y Livin only 20 minutes from Key West in the Florida Keys
House
Cudjoe Key, FL, 33042, United States
0.7k from Cutthroat Harbor Estates center

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

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$454
Average price / night
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ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!
ARTIST HOUSE ~ Canal Front 4 BR/3.5 Ba Home w/ Pool & Ocean and Gulf Access!
House
Cudjoe Key, FL, 33042, United States
0.7k from Cutthroat Harbor Estates center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$414
Average price / night
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Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage
Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage
House
Cudjoe Key, FL, 33042, United States
0.7k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
New to Booking
$293
Average price / night
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Beautiful 3BR/3BA Canal Home with Pool, Modern Upgrades, Dock for 28' Boat, Fenced Backyard
Beautiful 3BR/3BA Canal Home with Pool, Modern Upgrades, Dock for 28' Boat, Fenced Backyard
House
Cudjoe Key, FL, 33042, United States
0.7k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
New to Booking
$451
Average price / night
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Oceanside, heated pool, near Key West, space for 20-25 ft boat.  Book fall 2025!
Oceanside, heated pool, near Key West, space for 20-25 ft boat. Book fall 2025!
House
Cudjoe Key, FL, 33042, United States
0.7k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
10.0

Exceptional

13 reviews

$325
Average price / night
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NEPTUNES END - 4 Bedrooms / 3 Bathrooms Waterfront Retreat-  Pool & Sunset Views
NEPTUNES END - 4 Bedrooms / 3 Bathrooms Waterfront Retreat- Pool & Sunset Views
House
Cudjoe Key, FL, 33042, United States
0.7k from Cutthroat Harbor Estates center

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

4 Bedrooms12 Guests
9.2

Superb

9 reviews

$453
Average price / night
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Waterfront Relaxation and Barefoot Sunsets
Waterfront Relaxation and Barefoot Sunsets
House
Cudjoe Key, FL, 33042, United States
0.8k from Cutthroat Harbor Estates center

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

2 Bedrooms4 Guests
9.6

Exceptional

13 reviews

$310
Average price / night
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Looking for a place to stay?
Looking for a place to stay?
House
Cudjoe Key, FL, 33042, United States
0.8k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
10.0

Exceptional

51 reviews

$255
Average price / night
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Foster's Folly | Gorgeous canalfront pool home
Foster's Folly | Gorgeous canalfront pool home
House
Summerland Key, FL, 33042, United States
0.8k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
6.0

Review score

1 reviews

$351
Average price / night
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Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
House
Cudjoe Key, FL, 33042, United States
0.8k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$555
Average price / night
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Waterfront, Heated-chilled pool, Outdoor kitchen, downstairs bathroom w/ shower!
Waterfront, Heated-chilled pool, Outdoor kitchen, downstairs bathroom w/ shower!
House
cudjoe key, FL, 33042, United States
0.9k from Cutthroat Harbor Estates center

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

3 Bedrooms6 Guests
9.6

Exceptional

18 reviews

$376
Average price / night
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Lower Keys Escape
Lower Keys Escape
Apartment
Summerland Key, FL, 33042, United States
0.9k from Cutthroat Harbor Estates center

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

10.0

Exceptional

1 reviews

$107
Average price / night
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Gorgeous Newer Oceanfront Home! Private heated pool, dock and great views!
Gorgeous Newer Oceanfront Home! Private heated pool, dock and great views!
House
Cudjoe Key, FL, 33042, United States
0.9k from Cutthroat Harbor Estates center

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

4 Bedrooms8 Guests
9.6

Exceptional

15 reviews

$700
Average price / night
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Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
House
Cudjoe Key, FL, 33042, United States
0.9k from Cutthroat Harbor Estates center

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

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$401
Average price / night
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BLUE PEARL - 5 Bedroom/ 4 Bathroom Pool, Kayak, Bike, Canal Front w/ Boat Lift
BLUE PEARL - 5 Bedroom/ 4 Bathroom Pool, Kayak, Bike, Canal Front w/ Boat Lift
House
Cudjoe Key, FL, 33042, United States
0.9k from Cutthroat Harbor Estates center

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

5 Bedrooms12 Guests
9.6

Exceptional

4 reviews

$648
Average price / night
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CASA AQUA - 16 Acre Open Water Spanish Style Casual Elegance
CASA AQUA - 16 Acre Open Water Spanish Style Casual Elegance
House
Cudjoe Key, FL, 33042, United States
1.1k from Cutthroat Harbor Estates center

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

5 Bedrooms15 Guests
9.6

Exceptional

61 reviews

$2145
Average price / night
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Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock
Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock
House
Summerland Key, FL, 33042, United States
1.1k from Cutthroat Harbor Estates center

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

2 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$744
Average price / night
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The Grand Tiki Estate - Private Dock, Pool & Endless Ocean Views
The Grand Tiki Estate - Private Dock, Pool & Endless Ocean Views
House
Cudjoe Key, FL, 33042, United States
2.1k from Cutthroat Harbor Estates center

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

4 Bedrooms8 Guests
New to Booking
$784
Average price / night
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Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
House
Summerland, FL, 33042, United States
2.1k from Cutthroat Harbor Estates center

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

5 Bedrooms12 Guests
9.6

Exceptional

80 reviews

$806
Average price / night
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Beautiful Oceanfront Villa with Pool and near Key West, Florida
Beautiful Oceanfront Villa with Pool and near Key West, Florida
Villa
Summerland Key, FL, 33042, United States
2.1k from Cutthroat Harbor Estates center

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

2 Bedrooms5 Guests
New to Booking
$621
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 Private Pool in Cutthroat Harbor Estates.

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Cutthroat Harbor Estates Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 112 verified vacation rentals with a private pool in Cutthroat Harbor Estates. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Cutthroat Harbor Estates vary depending on the property size, location, and travel season. Rates typically start from around $107 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 Cutthroat Harbor Estates also welcome pets. Currently, 31 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 Cutthroat Harbor Estates often include additional features such as Kitchen, Laundry, and Balcony/Terrace. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Cutthroat Harbor Estates 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.