Vacation Rentals with Pool in Grand Cayman, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Pensacola
  6.  Grand Cayman

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42 Best Vacation Rentals with Pool in Grand Cayman (Starting from $95)

Pensacola Retreat with Pool Access, 20 Mi to Beach
Pensacola Retreat with Pool Access, 20 Mi to Beach
House
Pensacola, FL, USA
2.3k from Grand Cayman center

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

3 Bedrooms6 Guests
New to Booking
$263
Average price / night
Check Availability
Luxury Townhome - Pool Access - Fast WiFi - Near Beaches & Shopping
Luxury Townhome - Pool Access - Fast WiFi - Near Beaches & Shopping
House
Pensacola, FL, 32534, United States
2.2k from Grand Cayman center

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

4 Bedrooms7 Guests
10.0

Exceptional

5 reviews

$209
Average price / night
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LUXURY TOWNHOME NEAR DOWNTOWN AND PENSACOLA BEACH
LUXURY TOWNHOME NEAR DOWNTOWN AND PENSACOLA BEACH
Apartment
Grand Cayman, Pensacola, Florida, USA
2.4k from Grand Cayman center

Apartments, Luxury, Cheap, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.6

Exceptional

18 reviews

$95
Average price / night
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Cheerful 3-bedroom Townhouse - Centrally Located
Cheerful 3-bedroom Townhouse - Centrally Located
House
Pensacola, FL, 32534, United States
2.5k from Grand Cayman center

AC, Dryer, Extra Bed, Internet, Laundry, No Smoking, Pool, Washer

4 Bedrooms10 Guests
5.0

Review score

2 reviews

$191
Average price / night
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morii - townhome with pool
morii - townhome with pool
Apartment
Pensacola, FL, USA
2.5k from Grand Cayman center

Apartments, Accommodations, Pools, Parking, Lodgings, Places to stay, Family

3 Bedrooms6 Guests
New to Booking
$170
Average price / night
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Minutes from white sand and blue seas! 3BR/2.5BA
Minutes from white sand and blue seas! 3BR/2.5BA
House
Pensacola, FL, 32534, United States
2.8k from Grand Cayman center

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

3 Bedrooms6 Guests
10.0

Exceptional

8 reviews

$208
Average price / night
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The Pearl
The Pearl
House
Pensacola, FL, USA
2.5k from Grand Cayman center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

2 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$500
Average price / night
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Private Oasis with Pool & Tiki Bar
Private Oasis with Pool & Tiki Bar
House
Pensacola, FL, 32514, United States
3.4k from Grand Cayman center

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

4 Bedrooms8 Guests
New to Booking
$384
Average price / night
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Landing Apartments - North Central Pensacola
Landing Apartments - North Central Pensacola
Apartment
Pine Forest, FL, USA
2.6k from Grand Cayman center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$199
Average price / night
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Back yard Oasis Pensacola
Back yard Oasis Pensacola
House
Pensacola, FL, 32534, United States
3.8k from Grand Cayman center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$354
Average price / night
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Jan's Oasis Family Retreat Pool Bar Games & Fun
Jan's Oasis Family Retreat Pool Bar Games & Fun
House
Pensacola, FL, USA
3.4k from Grand Cayman center

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

1 Bedroom8 Guests
New to Booking
$497
Average price / night
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Perfect 4-bedroom house with a Heated Pool in a nice Pensacola neighborhood
Perfect 4-bedroom house with a Heated Pool in a nice Pensacola neighborhood
House
Pensacola, FL, 32503, United States
4.0k from Grand Cayman center

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

4 Bedrooms9 Guests
8.0

Good

1 reviews

$318
Average price / night
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Pensacola Luxury Hideway
Pensacola Luxury Hideway
Villa
FL, USA
4.5k from Grand Cayman center

Balcony/Terrace, Air Conditioner, Pool, Parking, Internet, Child Friendly

2 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$100
Average price / night
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Quiet & Cozy Family Home! Perfect Winter Stay!
Quiet & Cozy Family Home! Perfect Winter Stay!
House
Pensacola, FL, 32526, United States
5.2k from Grand Cayman center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

6 reviews

$552
Average price / night
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The Lake House, Pool, Dock and Lake Access, Pensacola
The Lake House, Pool, Dock and Lake Access, Pensacola
House
Ferry Pass, FL, USA
5.0k from Grand Cayman center

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

2 Bedrooms4 Guests
New to Booking
$377
Average price / night
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Family Pool Home w/ Private Saltwater Pool
Family Pool Home w/ Private Saltwater Pool
House
Pensacola, FL, 32534, United States
5.3k from Grand Cayman center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$390
Average price / night
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Landing Apartments Pensacola - Belleview Heights
Landing Apartments Pensacola - Belleview Heights
Apartment
Bellview, FL, USA
6.0k from Grand Cayman center

Apartments, Accommodations, Pools, Parking, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$139
Average price / night
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Beautiful Home w/ Heated Pool & All the Comforts
Beautiful Home w/ Heated Pool & All the Comforts
House
Pensacola, FL, 32526, United States
5.5k from Grand Cayman center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$407
Average price / night
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Swim, Golf and Relax Family-Friendly Pensacola Gem
Swim, Golf and Relax Family-Friendly Pensacola Gem
House
Pensacola, FL, USA
6.3k from Grand Cayman center

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

3 Bedrooms8 Guests
New to Booking
$200
Average price / night
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Cozy Beachy Riverwalk Condo – Close to Downtown & Beaches
Cozy Beachy Riverwalk Condo – Close to Downtown & Beaches
Condo
Pensacola, FL, 32504, United States
5.7k from Grand Cayman center

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

1 Bedroom3 Guests
New to Booking
$168
Average price / night
Check Availability
Visit Pensacola
Visit Pensacola
House
Pensacola, FL, 32514, United States
5.7k from Grand Cayman center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Pool, Washer

5 Bedrooms11 Guests
New to Booking
$405
Average price / night
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Private Getaway with Screened Pool, Upscale Kitchen, & Large Private Fenced Yard
Private Getaway with Screened Pool, Upscale Kitchen, & Large Private Fenced Yard
House
Pensacola, FL, 32514, United States
6.1k from Grand Cayman center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

18 reviews

$346
Average price / night
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Pensacola's Pool Home hideaway
Pensacola's Pool Home hideaway
House
Pensacola, FL, 32526, United States
6.3k from Grand Cayman center

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

4 Bedrooms12 Guests
9.6

Exceptional

10 reviews

$493
Average price / night
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Swim, Golf & Relax! 'Kokomo on the Emerald Coast'
Swim, Golf & Relax! 'Kokomo on the Emerald Coast'
House
Pensacola, FL, 32514, United States
6.3k from Grand Cayman center

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

3 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$331
Average price / night
Check Availability
Game, Swim & Explore: Family Home in Pensacola
Game, Swim & Explore: Family Home in Pensacola
House
Pensacola, FL, 32505, United States
6.5k from Grand Cayman center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms12 Guests
New to Booking
$366
Average price / night
Check Availability
Fabulous, cozy cottage, w Hot Tub, 20-25 mins to Pensacola & Perdido Key Beach
Fabulous, cozy cottage, w Hot Tub, 20-25 mins to Pensacola & Perdido Key Beach
House
Pensacola, FL, 32505, United States
7.1k from Grand Cayman center

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

3 Bedrooms6 Guests
9.6

Exceptional

23 reviews

$195
Average price / night
Check Availability
Foosball Games & Al Fresco Dining: Pensacola Home!
Foosball Games & Al Fresco Dining: Pensacola Home!
House
Pensacola, FL, 32514, United States
7.2k from Grand Cayman center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, No Smoking, Outdoor Space, Patio

3 Bedrooms8 Guests
8.8

Fabulous

3 reviews

$333
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 Grand Cayman.

Stay Near Grand Cayman's Top Attractions

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

Grand Cayman Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 42 verified vacation rentals with a pool in Grand Cayman. 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 Grand Cayman vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $95 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Grand Cayman 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 Grand Cayman welcome pets. Currently, 13 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 Grand Cayman often include additional outdoor features such as Pool, Fireplace/Heating, and Internet. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Grand Cayman 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.