Search Upper Matecumbe Key Condo Resort Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov
In one month
28 Nov - 30 Nov
In two months
26 Dec - 28 Dec

Featured Condo Resorts in Upper Matecumbe Key and around

We don't have any properties that match your exact search
See all properties in Upper Matecumbe Key

Recommended hotels in Upper Matecumbe Key

Private beach, white sand, sun-loungers, beach towels
Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 star property
9.2 out of 10, Wonderful, (1550)
"Wonderful property, breakfast was awesome "
United States
Carl
The price is €168
includes taxes & fees
3 Nov - 4 Nov
Chesapeake Beach Resort
Private beach, fishing
La Jolla Resort
La Jolla Resort
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Excellent motel"
United States
heidy
La Jolla Resort
Exterior
Breezy Palms Resort
Breezy Palms Resort
2.5 star property
8.8 out of 10, Excellent, (552)
"Spacious rooms and location was great for what we needed. "
United States
Daniel
The price is €99
includes taxes & fees
11 Nov - 12 Nov
Breezy Palms Resort
Exterior
Amara Cay Resort
Amara Cay Resort
4.0 star property
8.8 out of 10, Excellent, (1274)
"Great hotel with a perfect location and friendly staff."
United States
Amir
The price is €208
includes taxes & fees
30 Nov - 1 Dec
Amara Cay Resort
Private beach, sun-loungers, beach umbrellas, beach towels
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5.0 star property
9.2 out of 10, Wonderful, (1267)
"This resort was amazing!"
United States
Paul
The price is €253
includes taxes & fees
20 Nov - 21 Nov
Cheeca Lodge & Spa
Exterior
Islander Resort
Islander Resort
4.0 star property
9.2 out of 10, Wonderful, (1013)
"Staff at resort were extremely friendly and helpful. Highly recommend if visiting Islamorada"
United States
Thalia
The price is €254
includes taxes & fees
1 Dec - 2 Dec
Islander Resort
Outdoor pool, free pool cabanas
Sunset Inn
Sunset Inn
3.0 star property
9.4 out of 10, Exceptional, (1004)
"Conveniently located to dining options and attractions to explore and do."
United States
Tony
The price is €101
includes taxes & fees
2 Nov - 3 Nov
Sunset Inn
Outdoor pool, pool loungers
La Siesta Resort & Villas
La Siesta Resort & Villas
4.0 star property
8.6 out of 10, Excellent, (1002)
"Clean rooms, great ambiance and service. Would definitely go again!!"
United States
Gary
The price is €202
includes taxes & fees
30 Nov - 1 Dec
La Siesta Resort & Villas
Dock
Hadley Resort and Marina
Hadley Resort and Marina
3.5 star property
7.8 out of 10, Good, (1001)
"Super "
United States
Michel
The price is €133
includes taxes & fees
4 Nov - 5 Nov
Hadley Resort and Marina
Restaurant
Bayside Villas by Islander Resort
Bayside Villas by Islander Resort
3.5 star property
8.8 out of 10, Excellent, (391)
"The property was quiet and clean"
United States
Leah
The price is €250
includes taxes & fees
20 Nov - 21 Nov
Bayside Villas by Islander Resort
Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio
Sands of Islamorada
Sands of Islamorada
2.5 star property
8.8 out of 10, Excellent, (389)
"Nicely renovated older, smaller hotel with friendly staff that accommodates different arrival and departure times. Very clean, could have a better kitchen area, but comfortable stay!"
United States
Callie
The price is €157
includes taxes & fees
2 Nov - 3 Nov
Sands of Islamorada
Beach nearby, white sand, sun-loungers, beach umbrellas
Casa Morada
Casa Morada
3.5 star property
9.4 out of 10, Exceptional, (410)
"Beautiful"
United States
Zoila N
The price is €290
includes taxes & fees
2 Nov - 3 Nov
Casa Morada
Exterior
Pines & Palms Resort
Pines & Palms Resort
3.0 star property
9.2 out of 10, Wonderful, (1008)
"Very happy with accommodations. Simone at the Front Desk was amazing."
United States
Peter
Pines & Palms Resort
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers
The Islands of Islamorada
The Islands of Islamorada
4.0 star property
9.8 out of 10, Exceptional, (68)
"Beautiful property with great staff! "
United States
Ryan
The price is €728
includes taxes & fees
12 Nov - 13 Nov
The Islands of Islamorada
Pool
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
The price is €3,363
includes taxes & fees
8 Nov - 9 Nov
Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite
Pool
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
The price is €2,131
includes taxes & fees
8 Nov - 9 Nov
Private Hideaway w/ Balcony + Lush Views @Islamorada - Hideaway suite
Pool
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
The price is €2,227
includes taxes & fees
2 Dec - 3 Dec
Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite
Pool
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
The price is €1,835
includes taxes & fees
8 Nov - 9 Nov
Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite
Pool
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
The price is €1,806
includes taxes & fees
2 Dec - 3 Dec
Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite
Pool
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
The price is €1,683
includes taxes & fees
8 Nov - 9 Nov
Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upper Matecumbe Key Hotel Reviews

Rock Reef Resort

Rock Reef Resort

10/10 Excellent
"Our “cottage” was very cute and the updated condition was very nice. We enjoyed our stay and wish we could have stayed longer!"
Susan 1-night trip
Posted 4 days ago
Rock Reef Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Condo Resorts information

Number of reviews
Accommodation
 Condo Resorts
Lowest Price
Highest Price

Explore a world of travel with Expedia