Islamorada Resorts for Families

7 family-friendly resorts in Islamorada with pools, beachfront & kids' activities. Compare deals on Florida Keys family getaways now.

Check-in
Tue, 11 Aug
Check-out
Wed, 12 Aug
Rooms and Guests2 Guests, 1 room
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Check-in
Tue, 11 Aug
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Check-out
Wed, 12 Aug
Rooms and Guests2 Guests, 1 room
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Check-in
Tue, 11 Aug
-
Check-out
Wed, 12 Aug
Rooms and Guests2 Guests, 1 room
2Filter & Sort
View map
View map
1-7 out of 7
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  • Price: high to low
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8.3
Great816 total reviews
our site & Booking.com
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1246 yd from City Center131 yd from Anne s Beach
Fishing PierAdult PoolGolf Course
  • Longest fishing pier in Keys
  • Adults-only pool with butler
  • Jack Nicklaus golf course
FromUS$ 113 /nightSelect
8.6
Great624 total reviews
our site & Booking.com
Private BeachSwim-up BarWater Taxi
  • Adults-only cove with private beach
  • Keys' only swim-up bar
  • Complimentary water taxi included
FromUS$ 180 /nightSelect
8.6
Great288 total reviews
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Map
1.2 mi from City Center838 yd from Anne s Beach
Private PoolsShuttle ServiceFishing Dock
  • Two-bedroom townhouse with full kitchen
  • Full access to sister resort's pools
  • On-site fishing dock for anglers
FromUS$ 191 /nightSelect
8.5
Great937 total reviews
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1.2 mi from City Center231 yd from Islamorada
Private BeachHeated PoolComplimentary Kayaks
  • Guest-only private beach
  • Complimentary kayaks & paddleboards
  • Personalized breakfast delivery
FromUS$ 149 /nightSelect
9.0
Perfect1683 total reviews
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571 yd from City Center487 yd from Upper Matecumbe Key
Private BeachDiscovery CenterBayside Villas
  • Islamorada's largest private beach
  • On-site Florida Keys History Center
  • Bayside Villas with private pool
FromUS$ 204 /nightSelect
9.3
Perfect795 total reviews
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Map
2.0 mi from City Center1.3 mi from Anne s Beach
Private BeachHeated PoolTiki Bar
  • Complimentary kayaks and paddleboards
  • Private beach with sunset views
  • Old Florida-style cottages
FromUS$ 134 /nightSelect
9.2
Perfect172 total reviews
our site & Booking.com
Map
4.1 mi from City Center1.6 mi from Windley Key
Private MarinaHeated PoolWater Sports
  • Private marina for boaters
  • Heated pool with ocean views
  • Complimentary bikes and canoes
FromUS$ 360 /nightSelect

Islamorada offers a range of resorts tailored for families, from budget-friendly units with full kitchens to luxury properties with golf courses and spas. Most resorts feature multiple swimming pools, private beach access, and complimentary water sports like kayaking and paddleboarding. The area is ideal for families seeking a mix of relaxation and active outings, with attractions such as Theater of the Sea and fishing charters nearby. Expect to pay mid-range to premium rates, with many properties offering family rooms and on-site dining that accommodates all ages.

Among the top-rated options, Cheeca Lodge & Spa provides a 525-foot fishing pier, a nine-hole golf course, and supervised kids' programs, while Islander Resort boasts two family-sized pools and a private beach with a tiki bar. Three Waters Resort & Marina includes 12 dining venues and separate adult-only and family zones, plus free water taxi rides. For families wanting kitchen-equipped accommodations, Pines & Palms Resort offers oceanfront suites with full kitchens and barbecue cabanas. Bayside Villas by Islander Resort provides townhouse-style units with laundry facilities, perfect for longer stays. Book early during peak seasons to secure family-friendly suites.