Vacation Rentals with Private Pool in Plantation by the Sea, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Islamorada
  6.  Plantation by the Sea

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155 Best Vacation Rentals with Private Pool in Plantation by the Sea (Starting from $220)

Reel Key Largo Escape Ocean Pointe 5209
Reel Key Largo Escape Ocean Pointe 5209
House
Tavernier, FL, USA
8.2k from Plantation by the Sea center

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

2 Bedrooms4 Guests
9.4

Superb

5 reviews

$288
Average price / night
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Private Expansive Oceanfront 5 Bedroom Estate, Private Pier and Saltwater Pool
Private Expansive Oceanfront 5 Bedroom Estate, Private Pier and Saltwater Pool
House
Islamorada, FL, 33036, United States
0.4k from Plantation by the Sea center

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

5 Bedrooms12 Guests
10.0

Exceptional

66 reviews

$1486
Average price / night
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Brand New Unique Deep Water Gulf Front Estate.  Beach, Pool, Hot tub and docks
Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks
House
Islamorada, FL, 33070, United States
0.4k from Plantation by the Sea center

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

4 Bedrooms8 Guests
10.0

Exceptional

55 reviews

$2241
Average price / night
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Turtle Cove: Stunning 7-bedroom home in Islamorada with a private pool and open water views.
Turtle Cove: Stunning 7-bedroom home in Islamorada with a private pool and open water views.
House
Islamorada, FL, 33036, United States
0.4k from Plantation by the Sea center

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

7 Bedrooms16 Guests
New to Booking
$2493
Average price / night
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Beautiful Bayfront Home with Amazing Sunsets
Beautiful Bayfront Home with Amazing Sunsets
House
Islamorada, FL, 33036, United States
0.5k from Plantation by the Sea center

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

4 Bedrooms8 Guests
10.0

Exceptional

38 reviews

$785
Average price / night
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Spacious & Remodeled condo w/ sunset views!
Spacious & Remodeled condo w/ sunset views!
Apartment
Tavernier, FL, 33070, United States
0.9k from Plantation by the Sea center

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

3 Bedrooms6 Guests
New to Booking
$688
Average price / night
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Flamingo Bay: Stunning 6BR home with breathtaking open water views in Islamorada.
Flamingo Bay: Stunning 6BR home with breathtaking open water views in Islamorada.
House
Islamorada, FL, 33036, United States
1.0k from Plantation by the Sea center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Living Area

6 Bedrooms12 Guests
New to Booking
$1289
Average price / night
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5 Star Modern Oceanfront Islamorada Townhome on the Beach!
5 Star Modern Oceanfront Islamorada Townhome on the Beach!
House
Islamorada, FL, 33036, United States
1.0k from Plantation by the Sea center

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

2 Bedrooms4 Guests
10.0

Exceptional

109 reviews

$387
Average price / night
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Keys Cozy Townhouse
Keys Cozy Townhouse
House
Islamorada, FL, 33036, United States
1.0k from Plantation by the Sea center

AC, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
8.8

Fabulous

3 reviews

$220
Average price / night
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Pineapple Beach
Pineapple Beach
House
Islamorada, FL, 33036, United States
1.1k from Plantation by the Sea center

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

5 Bedrooms10 Guests
9.2

Superb

10 reviews

$3201
Average price / night
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Enjoy a cozy stay at 169 Sebring Drive, Tavernier, with 3 bedrooms and a private pool.
Enjoy a cozy stay at 169 Sebring Drive, Tavernier, with 3 bedrooms and a private pool.
House
Tavernier, FL, 33070, United States
1.2k from Plantation by the Sea center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$287
Average price / night
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Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage
Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage
House
Islamorada, FL, 33036, United States
1.7k from Plantation by the Sea center

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

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$659
Average price / night
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Bayfront Home with Pool in Islamorada
Bayfront Home with Pool in Islamorada
House
Tavernier, FL, 33070, United States
1.7k from Plantation by the Sea center

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

5 Bedrooms9 Guests
10.0

Exceptional

2 reviews

$1144
Average price / night
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Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
House
Islamorada, FL, 33070, United States
1.7k from Plantation by the Sea center

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

4 Bedrooms10 Guests
9.4

Superb

107 reviews

$1126
Average price / night
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Bayfront Home In Florida Keys
Bayfront Home In Florida Keys
House
Tavernier, FL, 33070, United States
1.8k from Plantation by the Sea center

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

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$809
Average price / night
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Charming Ocean Front Pool Home with dockage & pool
Charming Ocean Front Pool Home with dockage & pool
Villa
Islamorada, FL, 33036, United States
2.0k from Plantation by the Sea center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$2100
Average price / night
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3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
3-bedroom cozy pool home in exclusive Venetian Shores, Islamorada .
House
Islamorada, FL, 33036, United States
2.2k from Plantation by the Sea center

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

3 Bedrooms6 Guests
New to Booking
$414
Average price / night
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NEW Luxury Modern Coastal Home in Islamorada
NEW Luxury Modern Coastal Home in Islamorada
House
Islamorada, FL, 33036, United States
2.2k from Plantation by the Sea center

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

4 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$518
Average price / night
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Bellavista: Luxurious 4-bedroom home with stunning open water views in Islamorada.
Bellavista: Luxurious 4-bedroom home with stunning open water views in Islamorada.
House
Islamorada, FL, 33036, United States
2.3k from Plantation by the Sea center

Balcony, Barbecue, Hot Tub, Kitchen, Living Area, Microwave, No Smoking, Patio, Pool

4 Bedrooms8 Guests
New to Booking
$1268
Average price / night
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Discover comfort at 139 Venetian Way, a spacious 4BR getaway in Islamorada.
Discover comfort at 139 Venetian Way, a spacious 4BR getaway in Islamorada.
House
Islamorada, FL, 33036, United States
2.3k from Plantation by the Sea center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$372
Average price / night
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Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option
Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option
House
Tavernier, FL, 33070, United States
2.3k from Plantation by the Sea center

AC, Balcony, Barbecue, Crib, Dryer, Internet, Kitchen, Laundry, Microwave

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$428
Average price / night
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Experience luxury at Salty B in Islamorada with private pool and canal views!
Experience luxury at Salty B in Islamorada with private pool and canal views!
House
Islamorada, FL, 33036, United States
2.5k from Plantation by the Sea center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$369
Average price / night
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Morada Breeze ~ 6 Bedroom Plantation Key Home with Pool & Dockage
Morada Breeze ~ 6 Bedroom Plantation Key Home with Pool & Dockage
House
Tavernier, FL, 33070, United States
2.6k from Plantation by the Sea center

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

6 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$690
Average price / night
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Luxury Waterfront Escape- Brand New Home In Venetian Shores
Luxury Waterfront Escape- Brand New Home In Venetian Shores
House
Islamorada, FL, 33036, United States
2.6k from Plantation by the Sea center

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

4 Bedrooms8 Guests
New to Booking
$719
Average price / night
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The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip
The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip
House
Islamorada, FL, 33036, United States
2.6k from Plantation by the Sea center

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

4 Bedrooms8 Guests
9.8

Exceptional

81 reviews

$675
Average price / night
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Luxurious 4BR home with open water views in Islamorada, perfect for families.
Luxurious 4BR home with open water views in Islamorada, perfect for families.
House
Islamorada, FL, 33036, United States
2.6k from Plantation by the Sea center

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

4 Bedrooms6 Guests
New to Booking
$624
Average price / night
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Casa Margarita Islamorada, Paradise awaits!!
Casa Margarita Islamorada, Paradise awaits!!
House
Tavernier, FL, 33070, United States
2.7k from Plantation by the Sea center

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

3 Bedrooms6 Guests
New to Booking
$332
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 Plantation by the Sea.

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Plantation by the Sea Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 155 verified vacation rentals with a private pool in Plantation by the Sea. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Plantation by the Sea vary depending on the property size, location, and travel season. Rates typically start from around $220 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 Plantation by the Sea also welcome pets. Currently, 17 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 Plantation by the Sea often include additional features such as Private Pool, Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Plantation by the Sea 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.