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

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  4.  Florida
  5.  Long Key

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48 Best Vacation Rentals with Private Pool in Long Key (Starting from $193)

Beautiful Pool Home Located in a Quiet Neighborhood
Beautiful Pool Home Located in a Quiet Neighborhood
House
Long Key, FL, 33001, United States
0.5k from Long Key center

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

2 Bedrooms6 Guests
New to Booking
$649
Average price / night
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3 Bedroom / 2.5 Bathroom Layton Home with Pool & Dockage
3 Bedroom / 2.5 Bathroom Layton Home with Pool & Dockage
House
Layton, FL, 33001, United States
0.6k from Long Key center

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

3 Bedrooms6 Guests
New to Booking
$428
Average price / night
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Private Waterfront Home, Heated Pool, Beach, Tiki w/Grill, Dock, Kayaks, Sunset
Private Waterfront Home, Heated Pool, Beach, Tiki w/Grill, Dock, Kayaks, Sunset
House
Long Key, FL, 33001, United States
0.8k from Long Key center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Fireplace, Free Parking, Heater

3 Bedrooms10 Guests
10.0

Exceptional

103 reviews

$1473
Average price / night
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Home w/ 2nd Story Pool & Spa w/ Open Water Views
Home w/ 2nd Story Pool & Spa w/ Open Water Views
House
Layton, FL, 33001, United States
0.9k from Long Key center

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

4 Bedrooms10 Guests
10.0

Exceptional

76 reviews

$1480
Average price / night
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Gulf Front Rendezvous Retreat, Outdoor Resorts
Gulf Front Rendezvous Retreat, Outdoor Resorts
House
Long Key, FL, 33001, United States
3.7k from Long Key center

AC, Barbecue, Dryer, Internet, Kitchen, Living Area, No Smoking, Patio, Pool

2 Bedrooms6 Guests
New to Booking
$193
Average price / night
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Turtle Crawl on Long Key Oceanfront Beachfront with dock and pool
Turtle Crawl on Long Key Oceanfront Beachfront with dock and pool
House
Long Key, FL, 33001, United States
4.1k from Long Key center

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

5 Bedrooms12 Guests
New to Booking
$2287
Average price / night
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Pelican Retreat at Outdoor Resorts
Pelican Retreat at Outdoor Resorts
House
Long Key, FL, 33001, United States
4.1k from Long Key center

AC, Dryer, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms6 Guests
New to Booking
$193
Average price / night
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Stunning 5BR open water view home in Long Key, perfect for groups of 10!
Stunning 5BR open water view home in Long Key, perfect for groups of 10!
House
Long Key, FL, 33001, United States
4.3k from Long Key center

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

5 Bedrooms10 Guests
New to Booking
$1185
Average price / night
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3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
3-bedroom, 3-bath Canal front home with private pool in Islamorada, Florida Keys
House
Islamorada, FL, 33036, United States
8.0k from Long Key center

AC, Dryer, Heater, Internet, Kitchen, Laundry, No Smoking, Patio, Pool

3 Bedrooms10 Guests
New to Booking
$384
Average price / night
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A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
House
Islamorada, FL, 33036, United States
8.0k from Long Key center

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

3 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$571
Average price / night
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Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
House
Islamorada, FL, 33036, United States
8.1k from Long Key center

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

6 Bedrooms12 Guests
10.0

Exceptional

21 reviews

$668
Average price / night
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You will never want to leave
You will never want to leave
House
Islamorada, FL, 33036, United States
8.1k from Long Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1031
Average price / night
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\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
\"Our Happy Place\" Paradise in Islamorada with Heated Pool and 90 ft Dock
House
Islamorada, FL, 33036, United States
8.1k from Long Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$495
Average price / night
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Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access
Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access
House
Islamorada, FL, 33036, United States
8.3k from Long Key center

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

5 Bedrooms12 Guests
10.0

Exceptional

72 reviews

$1052
Average price / night
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Beautiful 4/3, pool home in lovely White Marlin beach, Islamorada, FL
Beautiful 4/3, pool home in lovely White Marlin beach, Islamorada, FL
House
Islamorada, FL, 33036, United States
8.5k from Long Key center

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

4 Bedrooms8 Guests
10.0

Exceptional

21 reviews

$586
Average price / night
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ISLAMORADA DREAM
ISLAMORADA DREAM
House
Islamorada, FL, 33036, United States
8.6k from Long Key center

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

4 Bedrooms8 Guests
New to Booking
$770
Average price / night
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The Octopus house is a new fabulous water front home in Marathon / Conch Key Fl
The Octopus house is a new fabulous water front home in Marathon / Conch Key Fl
House
Marathon, FL, 33050, United States
8.7k from Long Key center

AC, Balcony, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
New to Booking
$498
Average price / night
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Islamorada Boaters Paradise with 70' Dock and private beach access..
Islamorada Boaters Paradise with 70' Dock and private beach access..
House
Islamorada, FL, 33036, United States
8.7k from Long Key center

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

5 Bedrooms10 Guests
9.8

Exceptional

28 reviews

$974
Average price / night
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Private Beachfront Paradise
Private Beachfront Paradise
House
Islamorada, FL, 33036, United States
8.8k from Long Key center

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

4 Bedrooms8 Guests
9.6

Exceptional

81 reviews

$1054
Average price / night
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3200sqft Masterpiece Home, Fishing Paradise ,Waterfront, Beach, Pool, Islamorada
3200sqft Masterpiece Home, Fishing Paradise ,Waterfront, Beach, Pool, Islamorada
House
Islamorada, FL, 33036, United States
8.9k from Long Key center

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

4 Bedrooms8 Guests
9.8

Exceptional

20 reviews

$571
Average price / night
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🌴 Casa 157  @ White Marlin Beach
🌴 Casa 157 @ White Marlin Beach
House
Islamorada, FL, 33036, United States
8.9k from Long Key center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$461
Average price / night
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Perfect Home for a get away! Private homeowners beach,  enjoy Islamorada.
Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.
House
Islamorada, FL, 33036, United States
8.9k from Long Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$566
Average price / night
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Incredible Bayside Home in the Florida Keys!
Incredible Bayside Home in the Florida Keys!
House
Islamorada, FL, 33036, United States
8.9k from Long Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$387
Average price / night
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BRAND NEW Island-design home located in Islamorada fishing capital of the world!
BRAND NEW Island-design home located in Islamorada fishing capital of the world!
House
Islamorada, FL, 33036, United States
8.9k from Long Key center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$471
Average price / night
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New saltwater pool,  pet friendly, waterfront house with dock
New saltwater pool, pet friendly, waterfront house with dock
House
Islamorada, FL, 33036, United States
8.9k from Long Key center

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

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$441
Average price / night
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Beautiful two- story beach house
Beautiful two- story beach house
House
Islamorada, FL, 33036, United States
9.0k from Long Key center

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

4 Bedrooms10 Guests
New to Booking
$610
Average price / night
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NEW POOL ** Waterfront Paradise with Amazing Sunsets on Beach**
NEW POOL ** Waterfront Paradise with Amazing Sunsets on Beach**
House
Islamorada Village of Islands, FL, 33036, United States
9.0k from Long Key center

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

3 Bedrooms10 Guests
10.0

Exceptional

31 reviews

$513
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 Long Key.

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Long Key Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 48 verified vacation rentals with a private pool in Long 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 Long Key vary depending on the property size, location, and travel season. Rates typically start from around $193 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 Long Key also welcome pets. Currently, 18 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 Long Key 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 Long 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.