Vacation Rentals with Private Pool in Indian Key Historic State Park, FL: Compare 10+ Sites & Save

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  2. Vacation Rentals with Private Pool
  3.  USA

  4.  Florida
  5.  Indian Key Historic State Park

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97 Best Vacation Rentals with Private Pool in Indian Key Historic State Park (Starting from $202)

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
House
Islamorada, FL, 33036, United States
1.8k from Indian Key Historic State Park center

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

5 Bedrooms10 Guests
10.0

Exceptional

113 reviews

$1872
Average price / night
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Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool
Next available August 15th, 2026 - Stunning Oceanfront Estate - Private Pool
House
Islamorada, FL, 33036, United States
2.0k from Indian Key Historic State Park center

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

6 Bedrooms14 Guests
10.0

Exceptional

59 reviews

$2119
Average price / night
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Stunning 3-bedroom home in Islamorada with private heated pool and ocean views.
Stunning 3-bedroom home in Islamorada with private heated pool and ocean views.
House
Islamorada, FL, 33036, United States
2.1k from Indian Key Historic State Park center

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

3 Bedrooms6 Guests
New to Booking
$453
Average price / night
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Charming 3-Bedroom Canal Home in Islamorada with Private Pool & Balcony
Charming 3-Bedroom Canal Home in Islamorada with Private Pool & Balcony
House
Islamorada, FL, 33036, United States
2.4k from Indian Key Historic State Park center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$453
Average price / night
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Islamorada retreat \"Bungalow Blue\" w/ heated pool, Bikes, BBQ, amenities galore!
Islamorada retreat \"Bungalow Blue\" w/ heated pool, Bikes, BBQ, amenities galore!
House
Islamorada, FL, 33036, United States
2.4k from Indian Key Historic State Park center

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

2 Bedrooms4 Guests
10.0

Exceptional

23 reviews

$450
Average price / night
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Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
House
Islamorada, FL, 33036, United States
2.4k from Indian Key Historic State Park center

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

2 Bedrooms4 Guests
9.8

Exceptional

45 reviews

$426
Average price / night
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Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)
Ocean Side Condo In Paradise Mm 76.5-Islamorada, Fl (28 day minimum required)
Condo
Islamorada, FL, 33036, United States
2.5k from Indian Key Historic State Park center

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

1 Bedroom2 Guests
9.8

Exceptional

6 reviews

$202
Average price / night
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Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada
Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada
House
Islamorada, FL, 33036, United States
2.5k from Indian Key Historic State Park center

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

3 Bedrooms10 Guests
9.8

Exceptional

9 reviews

$433
Average price / night
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Relax in this 3BR open water view home with private pool in Islamorada.
Relax in this 3BR open water view home with private pool in Islamorada.
House
Islamorada, FL, 33036, United States
2.6k from Indian Key Historic State Park center

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

3 Bedrooms6 Guests
9.0

Fabulous

16 reviews

$686
Average price / night
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May 2nd - 9th available Oceanfront - Heated Pool - Dock
May 2nd - 9th available Oceanfront - Heated Pool - Dock
House
Islamorada, FL, 33036, United States
2.7k from Indian Key Historic State Park center

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

5 Bedrooms12 Guests
10.0

Exceptional

95 reviews

$1473
Average price / night
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Peninsula Villa | Boat Dock | Heated Pool | Sunset Point
Peninsula Villa | Boat Dock | Heated Pool | Sunset Point
House
Islamorada, FL, 33036, United States
2.8k from Indian Key Historic State Park center

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

5 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$2511
Average price / night
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Ocean  &  Bay Views.  Welcome To Paradise!
Ocean & Bay Views. Welcome To Paradise!
Condo
Islamorada, FL, 33036, United States
2.8k from Indian Key Historic State Park center

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

1 Bedroom2 Guests
10.0

Exceptional

36 reviews

$325
Average price / night
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PRIVATE BEACH, Pickleball Court and Tiki Bar/ Heated Pool / Designated Paradise Key
PRIVATE BEACH, Pickleball Court and Tiki Bar/ Heated Pool / Designated Paradise Key
House
Islamorada, FL, 33036, United States
2.9k from Indian Key Historic State Park center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Free Parking, Internet

6 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$4582
Average price / night
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Relax in this spacious 3BR home in Islamorada with a private pool!
Relax in this spacious 3BR home in Islamorada with a private pool!
House
Islamorada, FL, 33036, United States
2.9k from Indian Key Historic State Park center

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

3 Bedrooms6 Guests
New to Booking
$515
Average price / night
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Luxurious Home with POOL
Luxurious Home with POOL
House
Islamorada, FL, 33036, United States
2.9k from Indian Key Historic State Park center

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

3 Bedrooms8 Guests
10.0

Exceptional

41 reviews

$515
Average price / night
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Private Beach / Private overwater dock / Heated Pool / Mahi Key
Private Beach / Private overwater dock / Heated Pool / Mahi Key
House
Islamorada, FL, 33036, United States
3.2k from Indian Key Historic State Park center

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

3 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$3430
Average price / night
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Oceanfront Cottage With Stunning Pool & Dockage in Islamorada
Oceanfront Cottage With Stunning Pool & Dockage in Islamorada
Cottage
Islamorada, FL, 33036, United States
3.2k from Indian Key Historic State Park center

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

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$1588
Average price / night
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Caribee Beach House ~ Private Islamorada Beach Estate W/ Heated Pool & Dockage
Caribee Beach House ~ Private Islamorada Beach Estate W/ Heated Pool & Dockage
House
Islamorada, FL, 33036, United States
3.2k from Indian Key Historic State Park center

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

6 Bedrooms14 Guests
New to Booking
$2225
Average price / night
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Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
Villa
Islamorada, FL, 33060, United States
3.4k from Indian Key Historic State Park center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Elevator, Free Parking, Hot Tub, Internet

4 Bedrooms12 Guests
9.4

Superb

6 reviews

$2108
Average price / night
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Discover luxury in this 5-bedroom exquisite oceanfront pool home in beautiful Islamorada.
Discover luxury in this 5-bedroom exquisite oceanfront pool home in beautiful Islamorada.
House
Islamorada, FL, 33036, United States
3.7k from Indian Key Historic State Park center

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

5 Bedrooms10 Guests
10.0

Exceptional

45 reviews

$2095
Average price / night
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Stunning Oceanfront Home located in Islamorada Florida
Stunning Oceanfront Home located in Islamorada Florida
House
Lower Metecumbe, FL, 33036, United States
3.7k from Indian Key Historic State Park center

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

5 Bedrooms10 Guests
10.0

Exceptional

77 reviews

$2399
Average price / night
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Oceanfront 3 bedroom with dock
Oceanfront 3 bedroom with dock
House
Islamorada, FL, 33036, United States
3.8k from Indian Key Historic State Park center

AC, Barbecue, Breakfast Available, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$1175
Average price / night
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Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs
Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs
House
Islamorada, FL, 33036, United States
3.9k from Indian Key Historic State Park center

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

4 Bedrooms10 Guests
10.0

Exceptional

79 reviews

$1245
Average price / night
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Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada.
Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada.
House
Islamorada, FL, 33036, United States
4.2k from Indian Key Historic State Park center

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

4 Bedrooms10 Guests
8.4

Very Good

21 reviews

$1352
Average price / night
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Sandy Beach Cove🏝️🏖️  Gated Private Beach Home Plus Cottage Oasis , With Dock
Sandy Beach Cove🏝️🏖️ Gated Private Beach Home Plus Cottage Oasis , With Dock
House
Islamorada, FL, 33036, United States
4.5k from Indian Key Historic State Park center

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

4 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$747
Average price / night
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Beach Dream House, relax and enjoy the clear waters of Islamorada  FL
Beach Dream House, relax and enjoy the clear waters of Islamorada FL
House
Islamorada, FL, 33036, United States
4.6k from Indian Key Historic State Park center

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

2 Bedrooms6 Guests
10.0

Exceptional

49 reviews

$816
Average price / night
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One Ten Palms ~ Charming Islamorada Beachfront Home with Heated Pool
One Ten Palms ~ Charming Islamorada Beachfront Home with Heated Pool
House
Islamorada, FL, 33036, United States
4.8k from Indian Key Historic State Park center

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

3 Bedrooms10 Guests
New to Booking
$1482
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 Indian Key Historic State Park.

Where to stay in Indian Key Historic State Park? Best neighborhoods & areas

Indian Key Historic State Park Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 97 verified vacation rentals with a private pool in Indian Key Historic State Park. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Indian Key Historic State Park vary depending on the property size, location, and travel season. Rates typically start from around $202 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 Indian Key Historic State Park also welcome pets. Currently, 19 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 Indian Key Historic State Park often include additional features such as Kitchen, Laundry, and Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Indian Key Historic State Park 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.