Family-Friendly Vacation Rentals in Islamorada, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Islamorada

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126 Best Family Vacation Rentals in Islamorada (Starting from $183)

Beacon Reef 222
Beacon Reef 222
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$252
Average price / night
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BOOK YOUR DREAM VACATION at  BEACON REEF - SPECIAL MAY DEAL
BOOK YOUR DREAM VACATION at BEACON REEF - SPECIAL MAY DEAL
Condo
Islamorada, FL, 33036, United States
0.2k from Islamorada center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Heater

2 Bedrooms4 Guests
9.4

Superb

9 reviews

$321
Average price / night
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Beacon Reef 301
Beacon Reef 301
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$183
Average price / night
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Southern Diversion Estate  Islamorada
Southern Diversion Estate Islamorada
House
Islamorada, FL, 33036, United States
0.6k from Islamorada center

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

5 Bedrooms16 Guests
9.8

Exceptional

84 reviews

$2096
Average price / night
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Beacon Reef 306
Beacon Reef 306
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$192
Average price / night
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Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
Infinity Bay Islamorada ~ Luxury 9-bed, 10-bath Bayfront Estate in Islamorada
House
Islamorada, FL, 33036, United States
0.8k from Islamorada center

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

9 Bedrooms18 Guests
New to Booking
$2378
Average price / night
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Beacon Reef 307
Beacon Reef 307
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$197
Average price / night
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The Islands of Islamorada
The Islands of Islamorada
Villa
82779 Old Hwy, Islamorada, FL, 33036, United States
0.8k from Islamorada center

AC, Bar, Barbecue, Breakfast Available, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

1 Bedroom4 Guests
9.8

Exceptional

73 reviews

$841
Average price / night
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Beacon Reef 310
Beacon Reef 310
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$206
Average price / night
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Breathtaking ocean views for your Paradise vacations
Breathtaking ocean views for your Paradise vacations
Apartment
Islamorada, FL, 33036, United States
0.9k from Islamorada center

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

2 Bedrooms8 Guests
10.0

Exceptional

100 reviews

$464
Average price / night
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Beacon Reef 406
Beacon Reef 406
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$188
Average price / night
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Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!
House
Islamorada, FL, 33036, United States
1.1k from Islamorada center

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

5 Bedrooms10 Guests
10.0

Exceptional

84 reviews

$1494
Average price / night
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Beacon Reef 501
Beacon Reef 501
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$206
Average price / night
Check Availability
3‑Acre Oceanfront Estate w/ Pool ON the Atlantic, 2 Homes & Beach
3‑Acre Oceanfront Estate w/ Pool ON the Atlantic, 2 Homes & Beach
House
Islamorada, FL, 33036, United States
1.1k from Islamorada center

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

3 Bedrooms8 Guests
10.0

Exceptional

49 reviews

$1409
Average price / night
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Beacon Reef 503
Beacon Reef 503
House
Islamorada, FL, USA
0.3k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$256
Average price / night
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Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!
Sprawling Bayfront Estate in Heart of Islamorada with Deep Dockage, Heated Pool, Kayaks and More!
House
Islamorada, FL, 33036, United States
1.2k from Islamorada center

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

8 Bedrooms22 Guests
New to Booking
$3309
Average price / night
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Little Bay Prime
Little Bay Prime
Apartment
Islamorada, FL, USA
1.4k from Islamorada center

Apartments, Accommodations, Parking, Spa, Lodgings, Beach, Places to stay, Family

4 Bedrooms12 Guests
New to Booking
$1099
Average price / night
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Spacious Bayfront Home with Heated Pool, Deep Dockage, Kayaks and More
Spacious Bayfront Home with Heated Pool, Deep Dockage, Kayaks and More
House
Islamorada, FL, 33036, United States
1.2k from Islamorada center

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

4 Bedrooms10 Guests
10.0

Exceptional

11 reviews

$1302
Average price / night
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Little Bay Cottage
Little Bay Cottage
House
Islamorada, FL, USA
1.4k from Islamorada center

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

2 Bedrooms4 Guests
New to Booking
$550
Average price / night
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Charming Bayfront Cottage in Heart of Islamorada with Heated Pool, Deep Dockage, Kayaks & More
Charming Bayfront Cottage in Heart of Islamorada with Heated Pool, Deep Dockage, Kayaks & More
Cottage
Islamorada, FL, 33036, United States
1.2k from Islamorada center

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

2 Bedrooms6 Guests
10.0

Exceptional

19 reviews

$878
Average price / night
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Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More
Private Cottage on Bayfront Estate with Heated Pool, Deep Dockage, Kayaks and More
Cottage
Islamorada, FL, 33036, United States
1.2k from Islamorada center

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

2 Bedrooms6 Guests
10.0

Exceptional

15 reviews

$674
Average price / night
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Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.3k from Islamorada center

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

3 Bedrooms6 Guests
9.6

Exceptional

4 reviews

$631
Average price / night
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Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$638
Average price / night
Check Availability
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

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

3 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$635
Average price / night
Check Availability
Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!
Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!
House
Islamorada, FL, 33036, United States
1.4k from Islamorada center

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

3 Bedrooms6 Guests
10.0

Exceptional

25 reviews

$504
Average price / night
Check Availability
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Villa
Islamorada, FL, 33036, United States
1.4k from Islamorada center

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

2 Bedrooms4 Guests
9.8

Exceptional

40 reviews

$358
Average price / night
Check Availability
Villa located on the water\nFree marina, and trailer parking.
Villa located on the water\nFree marina, and trailer parking.
House
Islamorada, FL, 33036, United States
1.5k from Islamorada center

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

1 Bedroom4 Guests
9.8

Exceptional

60 reviews

$403
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 Islamorada.

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Islamorada Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 126 verified family-friendly vacation rentals in Islamorada. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Islamorada vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $183 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Islamorada 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 Islamorada 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 Islamorada often include amenities such as Wellness Facilities, Child Friendly, and 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.