Family Hotels in Islamorada

October 2026
4
November 2026

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Oct 9 - Oct 11
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Oct 16 - Oct 18

Family Hotels in Islamorada

1. Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
  • Children's club included
  • Childcare
  • 3 outdoor pools
  • Arcade/game room
$189
$286 total
includes taxes & fees
Oct 8 - Oct 9
Cheeca Lodge & Spa

2. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • 2 outdoor pools
$151
$226 total
includes taxes & fees
Oct 5 - Oct 6
Chesapeake Beach Resort

3. Islander Resort

Islander Resort
Matecumbe
  • Cribs/infant beds provided
  • 2 outdoor pools
$286
$395 total
includes taxes & fees
Oct 27 - Oct 28
Islander Resort

4. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
  • 3 outdoor pools
$130
$192 total
includes taxes & fees
Oct 18 - Oct 19
Lime Tree Bay Resort

5. Amara Cay Resort

Amara Cay Resort
Matecumbe
  • Cribs/infant beds provided
  • Outdoor pool
$155
$247 total
includes taxes & fees
Oct 18 - Oct 19
Amara Cay Resort

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
  • Cribs/infant beds provided
  • 3 outdoor pools
  • Arcade/game room
$215
$315 total
includes taxes & fees
Oct 18 - Oct 19
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

7. La Siesta Resort & Villas

La Siesta Resort & Villas
Matecumbe
  • Outdoor pool
$168
$262 total
includes taxes & fees
Nov 3 - Nov 4
La Siesta Resort & Villas

8. Breezy Palms Resort

Breezy Palms Resort
Matecumbe
  • Outdoor pool
$93
$120 total
includes taxes & fees
Oct 7 - Oct 8
Breezy Palms Resort

9. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
  • Cribs/infant beds provided
  • Outdoor pool
$127
$175 total
includes taxes & fees
Oct 12 - Oct 13
Fisher Inn Resort & Marina

10. The Caribbean Resort

The Caribbean Resort
Matecumbe
  • Outdoor pool
The Caribbean Resort

11. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
  • Cribs/infant beds provided
  • Outdoor pool
$324
$438 total
includes taxes & fees
Oct 18 - Oct 19
Bayside Villas by Islander Resort

12. The Islands of Islamorada

The Islands of Islamorada
Matecumbe
  • 2 outdoor pools
$580
$719 total
includes taxes & fees
Oct 7 - Oct 8
The Islands of Islamorada

13. La Jolla Resort

La Jolla Resort
Matecumbe
  • Outdoor pool
$107
$149 total
includes taxes & fees
Oct 7 - Oct 8
La Jolla Resort

14. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
  • Cribs/infant beds provided
  • Outdoor pool
$135
$185 total
includes taxes & fees
Oct 18 - Oct 19
Hadley Resort and Marina

15. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
  • Outdoor pool
$149
$168 total
includes taxes & fees
Oct 5 - Oct 6
Coconut Cove Resort and Marina

16. Pines & Palms Resort

Pines & Palms Resort
Matecumbe
  • Outdoor pool
$229
$313 total
includes taxes & fees
Oct 6 - Oct 7
Pines & Palms Resort

17. Drop Anchor

Drop Anchor
Islamorada
  • Outdoor pool
$136
$188 total
includes taxes & fees
Oct 5 - Oct 6
Drop Anchor

18. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
Key Largo
  • Free parking
  • Free WiFi
  • Connecting rooms available
  • Air conditioning
  • Laundry facilities
  • Non-smoking
$97
$110 total
includes taxes & fees
Oct 7 - Oct 8
The Pelican Key Largo Cottages

19. Reefhouse Resort & Marina

Reefhouse Resort & Marina
Key Largo
  • Cribs/infant beds provided
  • Outdoor pool
  • Arcade/game room
$219
$286 total
includes taxes & fees
Oct 5 - Oct 6
Reefhouse Resort & Marina

20. Waterside Suites & Marina

Waterside Suites & Marina
Key Largo
  • Outdoor pool
$123
$166 total
includes taxes & fees
Oct 5 - Oct 6
Waterside Suites & Marina
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Discover your perfect family-friendly hotel in Islamorada

Pool
Breakfast included
Water park
4 stars
All-inclusive

Family-friendly hotels with pools in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa
Matecumbe
$189
$286 total
includes taxes & fees
Oct 8 - Oct 9
Cheeca Lodge & Spa

Islander Resort

Islander Resort
Matecumbe
$286
$395 total
includes taxes & fees
Oct 27 - Oct 28
Islander Resort

La Jolla Resort

La Jolla Resort
Matecumbe
$107
$149 total
includes taxes & fees
Oct 7 - Oct 8
La Jolla Resort

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
$149
$168 total
includes taxes & fees
Oct 5 - Oct 6
Coconut Cove Resort and Marina

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$215
$315 total
includes taxes & fees
Oct 18 - Oct 19
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$127
$175 total
includes taxes & fees
Oct 12 - Oct 13
Fisher Inn Resort & Marina

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$135
$185 total
includes taxes & fees
Oct 18 - Oct 19
Hadley Resort and Marina

The Islands of Islamorada

The Islands of Islamorada
Matecumbe
$580
$719 total
includes taxes & fees
Oct 7 - Oct 8
The Islands of Islamorada

Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
Matecumbe
$324
$438 total
includes taxes & fees
Oct 18 - Oct 19
Bayside Villas by Islander Resort

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
$278
$368 total
includes taxes & fees
Oct 13 - Oct 14
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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Family-friendly hotels with free breakfast in Islamorada

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Islamorada
$215
$315 total
includes taxes & fees
Oct 18 - Oct 19
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
Islamorada
$127
$175 total
includes taxes & fees
Oct 12 - Oct 13
Fisher Inn Resort & Marina

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
$149
$168 total
includes taxes & fees
Oct 5 - Oct 6
Coconut Cove Resort and Marina

Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
$135
$185 total
includes taxes & fees
Oct 18 - Oct 19
Hadley Resort and Marina

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
$278
$368 total
includes taxes & fees
Oct 13 - Oct 14
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
$99
$143 total
includes taxes & fees
Oct 5 - Oct 6
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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Top neighborhoods in Islamorada

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.

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.

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.

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 beach with a wooden structure, clear blue sky, and dense green foliage.

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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A marina with boats docked, a motel, and a cafe.

Bud n' Mary's Dive Center

8.8/10 (504 reviews)
You can stroll along Bud n' Mary's Dive Center for relaxing water views when you're in Matecumbe. Hotels.com travelers also say the area is relaxing and has lots of nice beaches.
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An aerial view of a coastal area with a marina, tennis courts, a baseball field, and surrounding greenery.

Founders Park

8.8/10 (450 reviews)
Founders Park is 4.6 mi (7.4 km) from central Islamorada, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Islamorada County Park, just a short walk away.
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A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Florida Keys Brewing Co.

9.2/10 (520 reviews)
Matecumbe is home to Florida Keys Brewing Co., so why not stop by during your stay in Islamorada.
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Robbie’s of Islamorada

8.4/10 (15 reviews)
You can stroll along Robbie’s of Islamorada for relaxing water views when you're in Matecumbe.
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Islamorada County Park

8.8/10 (198 reviews)
Islamorada County Park is 4.5 mi (7.2 km) from central Islamorada, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here? Want to stretch your legs some more? Head to Founders Park, just a short walk away.
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Islamorada Brewery & Distillery

9.4/10 (8 reviews)
Matecumbe is home to Islamorada Brewery & Distillery, so why not stop by during your stay in Islamorada.
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Sunset Drive Beach

9.0/10 (91 reviews)
If you can't wait to get to the beach, you might enjoy a trip to Sunset Drive Beach located 8 mi (12.9 km) from central Islamorada. If you want to continue walking by the waves, head to Anne's 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.