Family-Friendly Vacation Rentals in Indian Key Historic State Park, FL: Compare 10+ Sites & Save

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  5.  Indian Key Historic State Park

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121 Best Family Vacation Rentals in Indian Key Historic State Park (Starting from $119)

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
Check Availability
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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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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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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Villa Riolo
Villa Riolo
House
Islamorada, FL, USA
2.6k from Indian Key Historic State Park center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay, Family

2 Bedrooms6 Guests
New to Booking
$218
Average price / night
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Beautiful water front home, private dock in Islamorada, World Fishing Capital
Beautiful water front home, private dock in Islamorada, World Fishing Capital
House
Islamorada, FL, 33036, United States
2.5k from Indian Key Historic State Park center

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

2 Bedrooms9 Guests
9.0

Fabulous

4 reviews

$191
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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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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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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A little Piece of Heaven to wash your worries away
A little Piece of Heaven to wash your worries away
House
Islamorada, FL, 33036, United States
2.6k from Indian Key Historic State Park center

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

2 Bedrooms6 Guests
10.0

Exceptional

62 reviews

$248
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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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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Palms 317
Palms 317
House
Islamorada, FL, USA
2.8k from Indian Key Historic State Park center

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

1 Bedroom3 Guests
New to Booking
$119
Average price / night
Check Availability
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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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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Waterfront / Ocean Access Canal / Kamp Key / Homes
Waterfront / Ocean Access Canal / Kamp Key / Homes
House
Islamorada, FL, 33036, United States
2.8k from Indian Key Historic State Park center

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

3 Bedrooms10 Guests
New to Booking
$573
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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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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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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CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.
CHARMING WATERFRONT OCEANSIDE CANAL HOME-LARGE PROTECTED DOCKAGE-WiFi-SMART TVs.
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
9.6

Exceptional

89 reviews

$443
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
Check Availability
Beautiful ocean front private beach 2-bedroom house gorgeous views Isla morada
Beautiful ocean front private beach 2-bedroom house gorgeous views Isla morada
Villa
Islamorada, FL, 33036, United States
3.1k from Indian Key Historic State Park center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$517
Average price / night
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Sandglass 4
Sandglass 4
House
Islamorada, FL, USA
5.1k from Indian Key Historic State Park center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Places to stay, Family

5 Bedrooms12 Guests
New to Booking
$640
Average price / night
Check Availability
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
Check Availability
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
Check Availability
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
Check Availability
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
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 Family Vacation Rentals in Indian Key Historic State Park.

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

Indian Key Historic State Park Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 121 verified family-friendly vacation rentals in Indian Key Historic State Park. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Indian Key Historic State Park vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $119 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Indian Key Historic State Park offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Indian Key Historic State Park are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Indian Key Historic State Park often include amenities such as Child Friendly, View, and Ocean View. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.