Family Hotels in Islamorada

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Nov 6 - Nov 7
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Nov 13 - Nov 15

Family Hotels in Islamorada

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
  • Children's club included
  • Childcare
  • 3 outdoor pools
  • Arcade/game room
9.2 out of 10, Wonderful, (1,508 reviews)
Youngsters flourish at this oceanfront paradise featuring a dedicated children's club, three sparkling pools, and supervised activities. Parents appreciate beachfront dining options, tennis courts, and spa treatments while kids explore playgrounds and game rooms under caring staff supervision.
The price is $181
$277 total
includes taxes & fees
Nov 19 - Nov 20
Cheeca Lodge & Spa
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
  • 2 outdoor pools
9.4 out of 10, Exceptional, (1,807 reviews)
The price is $151
$226 total
includes taxes & fees
Nov 10 - Nov 11
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
  • Cribs/infant beds provided
  • 2 outdoor pools
9.4 out of 10, Exceptional, (1,162 reviews)
Splashy days await at this beachfront hotel where mini golf, pickleball courts, and free bicycle rentals keep everyone entertained. Kids splash in dual outdoor pools while parents unwind in beach cabanas. Three oceanview restaurants and volleyball courts complete the perfect family getaway.
The price is $179
$275 total
includes taxes & fees
Nov 15 - Nov 16
Islander Resort
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
  • Cribs/infant beds provided
  • Outdoor pool
8.8 out of 10, Excellent, (1,326 reviews)
Splash into vacation mode at this beachfront resort where families explore private shores and delight in outdoor adventures. Kids gravitate toward the sun-splashed pool while parents appreciate kayaking excursions, snorkeling, and biking options along scenic coastal paths.
The price is $187
$283 total
includes taxes & fees
Nov 15 - Nov 16
Amara Cay Resort
A swimming pool area with lounge chairs and umbrellas, surrounded by palm trees.

5. Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
  • Cribs/infant beds provided
  • 3 outdoor pools
  • Arcade/game room
9.0 out of 10, Wonderful, (308 reviews)
Splash-happy youngsters discover aquatic adventures across three outdoor pools while parents unwind beneath swaying palms. This tropical family haven offers arcade games, complimentary bicycle rentals, beachfront relaxation, and water sports from kayaking to snorkeling.
The price is $207
$306 total
includes taxes & fees
Nov 29 - Nov 30
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Terrace/patio

6. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
  • 3 outdoor pools
9.4 out of 10, Exceptional, (1,576 reviews)
The price is $124
$184 total
includes taxes & fees
Nov 19 - Nov 20
Lime Tree Bay Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

7. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
  • Outdoor pool
9.0 out of 10, Wonderful, (780 reviews)
The price is $77
$138 total
includes taxes & fees
Nov 10 - Nov 11
Breezy Palms Resort
A group of people sitting by a swimming pool.

8. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
  • Cribs/infant beds provided
  • Outdoor pool
8.2 out of 10, Very good, (1,000 reviews)
Splash into an action-packed family adventure at this beachfront haven where kids delight in the gated pool while parents relax on sun loungers. Complimentary bicycles, kayaks, and fishing opportunities create memorable moments for all ages.
The price is $139
$189 total
includes taxes & fees
Nov 8 - Nov 9
Fisher Inn Resort & Marina
A bedroom with a bed, a nightstand, a dresser, a window with shutters, and a wardrobe.

9. The Caribbean Resort

The Caribbean Resort
3.5 star property
Matecumbe
  • Outdoor pool
10.0 out of 10, Exceptional, (181 reviews)
Family-friendly fun awaits at this waterside retreat, where kids splash in the gated outdoor pool while parents unwind in the hot tub. Premium TV channels entertain after days of complimentary bicycle adventures and nearby marina explorations.
The Caribbean Resort
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

10. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
  • Cribs/infant beds provided
  • Outdoor pool
9.0 out of 10, Wonderful, (468 reviews)
Waterfront family adventures await at this ocean-side retreat featuring a saltwater swimming pool with sun loungers and umbrellas. Children can explore kayaking, sailing, and fishing while parents unwind watching spectacular sunset bay views after a day of memory-making activities.
The price is $288
$397 total
includes taxes & fees
Nov 8 - Nov 9
Bayside Villas by Islander Resort
A small, brightly colored building with a green and white exterior, two pink chairs outside, and palm trees in the background.

11. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
  • Outdoor pool
8.6 out of 10, Excellent, (1,000 reviews)
Family adventures flourish at this upscale resort featuring a pristine private beach and sparkling outdoor pool. Kids love cycling around the lush grounds while parents appreciate spacious rooms and the helpful staff. Marine activities create unforgettable vacation memories.
The price is $172
$266 total
includes taxes & fees
Nov 15 - Nov 16
La Siesta Resort & Villas
A pool area with a white fence, palm trees, and a building with a white exterior and multiple windows.

12. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
  • Outdoor pool
9.2 out of 10, Wonderful, (1,001 reviews)
The price is $143
$189 total
includes taxes & fees
Nov 18 - Nov 19
La Jolla Resort
Two individuals in a swimming pool, each holding a large inflatable float.

13. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
  • Cribs/infant beds provided
  • Outdoor pool
7.6 out of 10, Good, (1,002 reviews)
Families flock to this waterfront retreat where children adore the outdoor playground and gated pool while parents appreciate the complimentary bicycle rentals. Located on a private beach, the hotel offers kayaking, fishing from the dock, and stunning ocean views from spacious rooms.
The price is $139
$189 total
includes taxes & fees
Nov 10 - Nov 11
Hadley Resort and Marina
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

14. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
  • Outdoor pool
9.0 out of 10, Wonderful, (305 reviews)
The price is $169
$190 total
includes taxes & fees
Nov 15 - Nov 16
Coconut Cove Resort and Marina
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

15. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
  • Outdoor pool
9.2 out of 10, Wonderful, (1,001 reviews)
The price is $215
$297 total
includes taxes & fees
Nov 15 - Nov 16
Pines & Palms Resort
A wooden play structure with a slide, surrounded by lush greenery and palm trees.

16. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
  • 2 outdoor pools
9.6 out of 10, Exceptional, (83 reviews)
The price is $760
$928 total
includes taxes & fees
Nov 30 - Dec 1
The Islands of Islamorada
A beach with palm trees, a thatched-roof hut, and beach chairs.

17. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
  • Outdoor pool
8.6 out of 10, Excellent, (1,000 reviews)
The price is $128
$178 total
includes taxes & fees
Nov 8 - Nov 9
Drop Anchor
A beach with palm trees, a dock, and a boat named "STYX".

18. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
  • Free parking
  • Free WiFi
  • Connecting rooms available
  • Air conditioning
  • Laundry facilities
  • Non-smoking
9.0 out of 10, Wonderful, (1,006 reviews)
The price is $111
$125 total
includes taxes & fees
Nov 29 - Nov 30
The Pelican Key Largo Cottages
A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

19. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
  • Cribs/infant beds provided
  • Outdoor pool
8.8 out of 10, Excellent, (416 reviews)
Splash into vacation mode at this waterfront haven where kids love the outdoor swimming pool while parents unwind on poolside loungers. Just steps from Indian Key Historic State Park, families appreciate the free cribs and rollaway beds in spacious, well-equipped rooms.
The price is $192
$230 total
includes taxes & fees
Nov 16 - Nov 17
Sands of Islamorada
A beach with thatched umbrellas, palm trees, and blue lounge chairs.

20. Reefhouse Resort & Marina

Reefhouse Resort & Marina
4.5 star property
Key Largo
  • Cribs/infant beds provided
  • Outdoor pool
  • Arcade/game room
9.2 out of 10, Wonderful, (1,563 reviews)
Splashing in the outdoor pool, playing volleyball on the private beach, and exploring the game room creates unforgettable family memories. Children delight in beachfront activities while parents appreciate the marina, three on-site restaurants, and proximity to John Pennekamp Coral Reef State Park.
The price is $219
$286 total
includes taxes & fees
Nov 29 - Nov 30
Reefhouse Resort & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Discover your perfect family-friendly hotel in Islamorada

Pool
Breakfast included

Family-friendly hotels with pools in Islamorada

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1508)
The price is $181
$277 total
includes taxes & fees
Nov 19 - Nov 20
Cheeca Lodge & Spa
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Family-friendly hotels with free breakfast in Islamorada

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.8 out of 10, Good, (1003)
The price is $98
$142 total
includes taxes & fees
Nov 17 - Nov 18
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top neighborhoods in Islamorada

A shark sculpture with a sign above it that reads "Islamorada Florida Keys".

Matecumbe

Matecumbe gives you the full Florida Keys experience without trying too hard. Snorkel crystal waters at Anne's Beach, grab a cold one at Florida Keys Brewing Co, or watch fishermen haul in their catch at Bud n' Mary's. The Hurricane Monument and Indian Key Historic State Park tell stories of this laid-back paradise, while the MoradaWay Arts District adds cultural flair. Waterfront tiki bars serve fresh mahi-mahi as the sun sets over Florida Bay. Most visitors stay in charming resorts with private beaches and pools, though vacation rentals offer more space. You'll need a car to explore properly, but many resort areas are perfectly walkable.

A clear blue sea with a sandy beach and a distant horizon.

Lower Matecumbe Beach

Lower Matecumbe Beach offers pristine Atlantic shorelines where powder-soft sand meets crystal-clear turquoise waters. Sunset Drive Beach and nearby Anne's Beach provide perfect spots for swimming and sunbathing in the shallow, calm waters. You'll discover scenic overlooks at mile markers, historic fishing piers extending into Florida Bay, and the popular Founder's Park with its recreational facilities. Waterfront seafood restaurants serve fresh mahi-mahi and key lime pie with stunning ocean views. Accommodations range from luxury beachfront resorts to intimate bed-and-breakfasts. Getting around requires a rental car, though the beachfront areas are highly walkable with bike-friendly roads.

A sunset over a palm tree-lined pier extending into calm waters.

Venetian Shores

Venetian Shores offers the Keys dream—canal-front homes with private docks where dolphins practically introduce themselves at breakfast. Spend your days boating from your backyard to snorkeling spots or fishing the flats between the Atlantic and Florida Bay. This upscale residential enclave lets you live like a local without the tourist crowds. You'll need wheels to explore nearby attractions like Founders Park and the History of Diving Museum. The neighborhood itself has no restaurants or shops—just peaceful streets lined with luxury vacation rentals featuring pools and tropical gardens. For dining out, a quick 5-10 minute drive takes you to Islamorada's waterfront eateries.

A beach with palm trees, lounge chairs, and a building with balconies.

Seabreeze Trailer Park

Seabreeze Trailer Park offers a laid-back slice of Florida Keys paradise without the resort price tag. You'll get direct beach access for swimming and snorkeling in crystal-clear waters. Nearby Founders Park and Windley Key Fossil Reef Geological State Park provide perfect day trips. Rain Barrel Village offers local shopping when you need a break from all that sunshine. Seafood restaurants and waterfront dining options are just a short drive away in Islamorada. While public transit is limited, having a rental car or golf cart makes exploring the surrounding Keys a breeze. The peaceful, no-frills atmosphere makes this spot ideal for travelers seeking an authentic Keys experience on a budget.

Top landmarks in Islamorada

A wooden deck with benches overlooking a clear blue sea.

Anne's Beach

7.8/10 (597 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Anne's Beach located 8.8 mi (14.1 km) from central Islamorada. If you want to continue walking by the waves, head to Sunset Drive Beach located nearby.
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About the destination

Visitors really like Islamorada, especially its seaside, entertainment, and seafood. Enjoy fun activities like fishing and diving. You can easily spend a relaxing day visiting Everglades National Park and Islamorada County Park. You might find that sights like Bud n' Mary's Dive Center and Robbie’s of Islamorada are worth a visit.