Find Beach Resorts in Upper Matecumbe Key, FL
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Upper Matecumbe Key Beach Resorts & Hotels
Tonight
3 Sept - 4 SeptTomorrow
4 Sept - 5 SeptThis weekend
4 Sept - 6 SeptNext weekend
11 Sept - 13 SeptOur top choices for Upper Matecumbe Key beach hotels
1. Chesapeake Beach Resort
Chesapeake Beach ResortMatecumbe
- Unwind on Islamorada's private white sand beach with loungers, boat tours, and spectacular sunset views just steps away
£138
includes taxes & fees
8 Sept - 9 Sept
2. Breezy Palms Resort
Breezy Palms ResortMatecumbe
- Sink your toes in soft sand steps away from this beachside resort with private marina.
£74
includes taxes & fees
7 Sept - 8 Sept
3. Pines & Palms Resort
Pines & Palms ResortMatecumbe
- Unwind where the Florida Keys meet paradise: private beach bliss with water sports, yoga, and endless ocean adventures.
£205
includes taxes & fees
9 Sept - 10 Sept
4. Casa Morada
Casa MoradaMatecumbe
- Escape to a serene beachside sanctuary with complimentary kayaking and a short drive to pristine white sands with loungers and umbrellas.
£146
includes taxes & fees
7 Sept - 8 Sept
5. Drift Hotel
Drift HotelKey Largo
- Experience waterfront bliss with direct beach access, kayaking adventures, and sandy shores perfect for unwinding in the Florida sun.
£30
includes taxes & fees
10 Sept - 11 Sept
6. Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dove Creek Resort & Marina, Trademark Collection by WyndhamKey Largo
- Relax by the marina, offering easy beach access with free shuttle to private beach club.
£105
includes taxes & fees
23 Sept - 24 Sept
7. Rock Reef Resort
Rock Reef ResortRock Harbor
- Seaside adventure on a private sandy beach with kayaking, beach towels, and a sun-drenched outdoor pool for coastal relaxation.
£91
includes taxes & fees
13 Sept - 14 Sept
8. Coconut Palm Inn
Coconut Palm InnTavernier
- Escape to a private white sand paradise with paddleboarding, kayaking, and breathtaking sunsets on the waterfront.
£186
includes taxes & fees
15 Sept - 16 Sept
View all properties
Top Upper Matecumbe Key Hotel Reviews
Lime Tree Bay Resort
10/10 Excellent
"Fantastic place to stay. Small family style resort. Old school flordia feel."
Waterside Suites & Marina
8/10 Good
"The room was okay. Nothing stood out about it. I didn't realize the bedroom was on the 2nd floor, and the steps are kind of narrow and steep. Maintenance could repair the blinds."
Pines & Palms Resort
10/10 Excellent
"Quiet, Matthew and JJ were extremely friendly and respectful. Thank you."
Chesapeake Beach Resort
10/10 Excellent
"A great place to stay and very well located. Breakfast staff was wonderful and very accommodating. Check in staff as well. A beautiful property,"
Amara Cay Resort
10/10 Excellent
"Baseboard were removed off the wall. Did not gave it a clean look . Walls in the hallway slightly dirty."
Islander Resort
8/10 Good
"In stay, so many activities near by"
Breezy Palms Resort
10/10 Excellent
"Espectacular y muy limpio"
Playa Largo Resort & Spa, Autograph Collection
10/10 Excellent
"Perfection!"
La Jolla Resort
10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️"
Explore a world of travel with Expedia
- 5 Star Hotels in Duck Key
- 5 Star Hotels in Islamorada
- 5 Star Hotels in Key Largo
- Boutique Hotels in Duck Key
- Hotels near Everglades National Park
- Flamingo Hotels
- Hotels near Harry Harris Park
- Luxury Hotels in Homestead
- Spa Hotels in Homestead
- Beach Resorts & in Islamorada
- Beautiful Home in a Great Neighborhood with Ocean Access and Boat Ramp on Property
- Cheap Hotels in Islamorada
- Family-Friendly Hotels in Islamorada
- Sleeps 8
- Hotels Suites in Islamorada
- Hotels with a Bar in Islamorada
- Hotels with Connecting Rooms in Islamorada
- Hotels with Hot Tubs in Islamorada
- Isla Honeydew
- Isla Lychee
- Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
- Bayside Villas by Islander Resort
- Luxury Hotels in Islamorada
- Three Waters Resort and Marina
- Islamorada Hotels
- Hotels near Jimmy Johnson's Big Chill
- 124 Mariners Club
- 200ft of Waterfront with Tiki & Heated Pool
- Spectacular Oceanfront Views 3 bed/bath Villa with Amazing Views!
- 3bed vacation ocean side townhome 2pools
- 403 Mariners Club
- All-Inclusive Hotels in Key Largo
- Beach Resorts & in Key Largo
- Mariners Club Townhouse
- Cheap Hotels in Key Largo
- Family-Friendly Hotels in Key Largo
- Florida Keys canal front Vacation Home
- Gay-Friendly Hotels in Key Largo
- Island Paradise with private beach & private bay sunset views.
- Kawama Yacht Club
- Key Largo 3 Bedroom Penthouse Condo with Boat Slip and Bay View
- Pennekamp Hideaway
- Full TIME LIC MGR
- Mariner's Club Key Largo by KeysCaribbean
- Oceanfront 2BR/2.5BA Mariner's Club Villa 512 with Oasis Pool
- Paradise Cove-1stFloor- Key Largo
- Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
- Private Beach Bayside 6 Bedroom Resort Home with Pool
- Reefhouse Resort & Marina
- Marina Vista Gem • Modern 2BR/2BA • Steps to Pickleball
- Sunrise Escape
- New! CASA AZUL OCEANSIDE
- Key Largo Hotels
- Layton Hotels
- Long Key Hotels
- Adults Only Resorts & in Marathon
- Beach Resorts & in Marathon
- Cheap Hotels in Marathon
- Hotels with Airport Transfers in Marathon
- Luxury Hotels in Marathon
- Matecumbe Hotels
- Key Largo Baha Penthouse Ocean Pointe 1416
- Modern and Coastal Ocean Pointe 2307
- Ocean Oasis at Ocean Pointe Key Largo Pool Jacuzzi Beach in a Safe Gated Resort
- New Ocean Pearl • Beach • Restaurant • Pickleball • Marina
- Whispering Palms
- Tavernier Hotels