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

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Florida
  5.  Indian Key Historic State Park

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199 Best Vacation Rentals with Pool in Indian Key Historic State Park (Starting from $128)

Castaway Island Vacation Bungalow
Castaway Island Vacation Bungalow
Villa
Islamorada, FL, USA
2.4k from Indian Key Historic State Park center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Bungalows

2 Bedrooms4 Guests
New to Booking
$560
Average price / night
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The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach
The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach
House
Islamorada, FL, 33036, United States
1.3k from Indian Key Historic State Park center

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

4 Bedrooms8 Guests
10.0

Exceptional

45 reviews

$937
Average price / night
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Key Lime Cottage in the heart of Islamorada
Key Lime Cottage in the heart of Islamorada
House
Indian Key Historic State Park, Florida, USA
2.4k from Indian Key Historic State Park center

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

2 Bedrooms5 Guests
9.3

Superb

3 reviews

$308
Average price / night
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The Snook House at Tarpon Point  ~ 4 Bed/4 Bath Oceanfront Home
The Snook House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home
House
Islamorada, FL, 33036, United States
1.3k from Indian Key Historic State Park center

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

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$1115
Average price / night
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Palms 301
Palms 301
House
Islamorada, FL, USA
2.8k from Indian Key Historic State Park center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach

2 Bedrooms6 Guests
New to Booking
$156
Average price / night
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Welcome to Our Beautiful Spacious 2 BR Home in the Heart of Islamorada, Florida
Welcome to Our Beautiful Spacious 2 BR Home in the Heart of Islamorada, Florida
House
Islamorada, FL, 33036, United States
1.4k from Indian Key Historic State Park center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Laundry, Microwave, No Smoking

2 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$501
Average price / night
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Palms 309
Palms 309
House
Islamorada, FL, USA
2.8k from Indian Key Historic State Park center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach

2 Bedrooms5 Guests
New to Booking
$174
Average price / night
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The Bonefish House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home
The Bonefish House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home
House
Islamorada, FL, 33036, United States
1.4k from Indian Key Historic State Park center

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

4 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$978
Average price / night
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Palms 313
Palms 313
House
Islamorada, FL, USA
2.8k from Indian Key Historic State Park center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Beach

2 Bedrooms5 Guests
New to Booking
$192
Average price / night
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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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Palms 417
Palms 417
House
Islamorada, FL, USA
2.8k from Indian Key Historic State Park center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Beach, Jacuzzis

1 Bedroom3 Guests
New to Booking
$128
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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Beach Residence Private overwater dock Heated Pool Mahi Key
Beach Residence Private overwater dock Heated Pool Mahi Key
House
Islamorada, FL, USA
2.9k from Indian Key Historic State Park center

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

3 Bedrooms6 Guests
New to Booking
$1282
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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Matecumbe Resort
Matecumbe Resort
Apartment
Islamorada, FL, USA
3.0k from Indian Key Historic State Park center

Apartments, Accommodations, Pools, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach, Places to stay

32 Bedrooms26 Guests
8.4

Very Good

332 reviews

$214
Average price / night
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 Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada
Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada
House
Islamorada, FL, 33036, United States
2.2k from Indian Key Historic State Park center

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

2 Bedrooms4 Guests
9.4

Superb

24 reviews

$410
Average price / night
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Pines & Palms Resort
Pines & Palms Resort
Resort
Indian Key Historic State Park, Florida, USA
3.6k from Indian Key Historic State Park center

Accommodations, Pools, Resorts, Parking, Romantic, 3-star, Lodgings, Beach, Places to stay

24 Bedrooms44 Guests
9.0

Fabulous

762 reviews

$282
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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Beachfront Villa at Islamorada BY THE GLAMHOMES
Beachfront Villa at Islamorada BY THE GLAMHOMES
Villa
Islamorada, FL, USA
3.8k from Indian Key Historic State Park center

Internet, View, Private Beach, Oceanfront, Sports/Activities, Ocean View, Fireplace/Heating

4 Bedrooms6 Guests
1.0

Review score

1 reviews

$7615
Average price / night
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TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
House
Islamorada, FL, 33036, United States
2.4k from Indian Key Historic State Park center

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

2 Bedrooms5 Guests
10.0

Exceptional

98 reviews

$660
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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Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat
Beautiful Ocean Access Islamorada Condo. MM 76.5 Bring your Boat
Condo
Islamorada, FL, 33036, United States
2.5k from Indian Key Historic State Park center

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

1 Bedroom5 Guests
8.8

Fabulous

5 reviews

$239
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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Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
House
Islamorada, FL, 33036, United States
2.5k from Indian Key Historic State Park center

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

2 Bedrooms4 Guests
9.6

Exceptional

19 reviews

$448
Average price / night
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Charming Condo in Paradise!
Charming Condo in Paradise!
Condo
Islamorada, FL, 33036, United States
2.5k from Indian Key Historic State Park center

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

1 Bedroom4 Guests
New to Booking
$184
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 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 Pool on the Map

Frequently Asked Questions

You can explore 199 verified vacation rentals with a pool in Indian Key Historic State Park. 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 Indian Key Historic State Park vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $128 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Indian Key Historic State Park 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 Indian Key Historic State Park welcome pets. Currently, 24 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 Indian Key Historic State Park often include additional outdoor features such as Pool, Wellness Facilities, and View. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Indian Key Historic State Park 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.