Vacation Rentals with Private Pool in Cudjoe Gardens, FL: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Cudjoe Key
  6.  Cudjoe Gardens

Refine your search

Price per night

Amenity Filter

Rating

95 Best Vacation Rentals with Private Pool in Cudjoe Gardens (Starting from $324)

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
0.0k from Cudjoe Gardens center

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

3 Bedrooms6 Guests
9.6

Exceptional

24 reviews

$336
Average price / night
Check Availability
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
0.3k from Cudjoe Gardens center

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

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$499
Average price / night
Check Availability
Private Secluded Ocean View & Pool Near Key West
Private Secluded Ocean View & Pool Near Key West
House
Summerland Key, FL, 33042, United States
0.3k from Cudjoe Gardens 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
Check Availability
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
0.3k from Cudjoe Gardens center

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

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$516
Average price / night
Check Availability
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
0.4k from Cudjoe Gardens center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$532
Average price / night
Check Availability
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
0.4k from Cudjoe Gardens center

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

3 Bedrooms6 Guests
New to Booking
$324
Average price / night
Check Availability
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
0.4k from Cudjoe Gardens center

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

3 Bedrooms8 Guests
New to Booking
$424
Average price / night
Check Availability
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
0.4k from Cudjoe Gardens center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$393
Average price / night
Check Availability
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
0.4k from Cudjoe Gardens center

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

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$463
Average price / night
Check Availability
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
0.5k from Cudjoe Gardens center

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

3 Bedrooms6 Guests
New to Booking
$486
Average price / night
Check Availability
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
0.5k from Cudjoe Gardens 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
0.5k from Cudjoe Gardens center

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

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$884
Average price / night
Check Availability
Villa Jekjak
Villa Jekjak
House
Summerland Key, FL, 33042, United States
0.5k from Cudjoe Gardens center

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

4 Bedrooms8 Guests
New to Booking
$407
Average price / night
Check Availability
Private Beach House w/Pool
Private Beach House w/Pool
House
Cudjoe Key, FL, 33042, United States
0.5k from Cudjoe Gardens 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
Check Availability
Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with Pool
Villa
125 Colson Dr, Summerland Key, FL, 33042, United States
0.7k from Cudjoe Gardens center

Barbecue, Business Services, Free Parking, Hot Tub, Internet, Kids Pool, Laundry, Living Area, No Smoking

10.0

Exceptional

2 reviews

$1096
Average price / night
Check Availability
Eco Friendly Secluded OceanView Pool near Key West
Eco Friendly Secluded OceanView Pool near Key West
Villa
Cudjoe Key, FL, 33042, United States
0.7k from Cudjoe Gardens center

AC, Barbecue, Heater, Kitchen, Living Area, No Smoking, Pool, TV, Washer

4 Bedrooms10 Guests
New to Booking
$979
Average price / night
Check Availability
Beachfront • Heated Pool • Hot Tub • Oceanview
Beachfront • Heated Pool • Hot Tub • Oceanview
Villa
Cudjoe Key, FL, 33042, United States
0.7k from Cudjoe Gardens center

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

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$947
Average price / night
Check Availability
White Home - Receive 400 dollars \ntowards a BOAT RENTAL!
White Home - Receive 400 dollars \ntowards a BOAT RENTAL!
House
Cudjoe Key, FL, 33042, United States
0.9k from Cudjoe Gardens center

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

4 Bedrooms8 Guests
10.0

Exceptional

207 reviews

$520
Average price / night
Check Availability
Blue Home - Receive 400 dollars \ntowards a BOAT RENTAL!
Blue Home - Receive 400 dollars \ntowards a BOAT RENTAL!
House
Cudjoe Key, FL, 33042, United States
0.9k from Cudjoe Gardens center

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

4 Bedrooms8 Guests
10.0

Exceptional

160 reviews

$492
Average price / night
Check Availability
Tropical Paradise - Ocean front with swim spa
Tropical Paradise - Ocean front with swim spa
House
Cudjoe Key, FL, 33042, United States
0.9k from Cudjoe Gardens center

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

3 Bedrooms8 Guests
9.6

Exceptional

90 reviews

$609
Average price / night
Check Availability
Fandango - private pool <br>This is a pet friendly home. A pet fee and approval of your pet is required.
Fandango - private pool <br>This is a pet friendly home. A pet fee and approval of your pet is required.
House
Cudjoe Key, FL, 33042, United States
0.9k from Cudjoe Gardens center

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

5 Bedrooms12 Guests
9.8

Exceptional

87 reviews

$800
Average price / night
Check Availability
Family Retreat Ocean front pool
Family Retreat Ocean front pool
House
Cudjoe Key, FL, 33042, United States
1.0k from Cudjoe Gardens center

AC, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry, No Smoking

5 Bedrooms14 Guests
9.4

Superb

91 reviews

$846
Average price / night
Check Availability
Blue Palms w/boat dock and saltwater pool.
Blue Palms w/boat dock and saltwater pool.
House
Cudjoe Key, FL, 33042, United States
1.1k from Cudjoe Gardens center

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

4 Bedrooms8 Guests
9.8

Exceptional

158 reviews

$579
Average price / night
Check Availability
Latitudes - Ocean front with salt water pool.
Latitudes - Ocean front with salt water pool.
House
Cudjoe Key, FL, 33042, United States
1.1k from Cudjoe Gardens center

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

6 Bedrooms12 Guests
9.8

Exceptional

45 reviews

$801
Average price / night
Check Availability
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
1.3k from Cudjoe Gardens center

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

4 Bedrooms8 Guests
New to Booking
$784
Average price / night
Check Availability
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
1.3k from Cudjoe Gardens 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
Check Availability
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
2.1k from Cudjoe Gardens center

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

5 Bedrooms15 Guests
9.6

Exceptional

61 reviews

$2145
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 Cudjoe Gardens.

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods

Stay Near Cudjoe Gardens's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Cudjoe Gardens Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 95 verified vacation rentals with a private pool in Cudjoe Gardens. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Cudjoe Gardens vary depending on the property size, location, and travel season. Rates typically start from around $324 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 Cudjoe Gardens also welcome pets. Currently, 32 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 Cudjoe Gardens often include additional features such as Laundry, Pool, and Private Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Cudjoe Gardens 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.