Best Condo Resort Rentals in Upper Matecumbe Key, FL from $98

Upper Matecumbe Key Condo Resorts
Islamorada
Florida
United States of America
Condo Resorts
Expedia.com

Upper Matecumbe Key Travel Guide Hotels in Upper Matecumbe Key Vacation Rentals in Upper Matecumbe Key Flights to Upper Matecumbe Key Car Rentals in Upper Matecumbe Key Upper Matecumbe Key Vacation Packages

A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A beach with palm trees and lounge chairs.

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

1. Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 star property

Matecumbe

9.2 out of 10, Wonderful, (1,795 reviews)

9.2/10

Wonderful

(1,795 reviews)

"Great place"

Richard

$187 nightly

The price is $211

$211 total

Oct 18 - Oct 19

Total with taxes and fees

Chesapeake Beach Resort

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

A wooden pier leading to a beach with palm trees and a row of beach huts.

A bar area with a wooden counter, bar stools, and potted plants.

A paved pathway leading to a beach with palm trees and a view of the ocean.

2. Islander Resort

Islander Resort

4.0 star property

Matecumbe

9.4 out of 10, Exceptional, (1,134 reviews)

9.4/10

Exceptional

(1,134 reviews)

"Amazing place would definitely recommend"

Steven

$305 nightly

The price is $343

$343 total

Oct 18 - Oct 19

Total with taxes and fees

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.

An aerial view of a resort with a swimming pool, palm trees, and a dock.

A resort pool with palm trees, beach chairs, and umbrellas.

A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

3. Amara Cay Resort

Amara Cay Resort

4.0 star property

Matecumbe

8.8 out of 10, Excellent, (1,319 reviews)

8.8/10

Excellent

(1,319 reviews)

"Super clean resort."

Danielle

$220 nightly

The price is $247

$247 total

Oct 18 - Oct 19

Total with taxes and fees

Amara Cay Resort

A beach with palm trees, thatched-roof huts, and lounge chairs.

A modern kitchen with a microwave, stove, and refrigerator. There is a dining area with a table and chairs.

A building facade with the text "Buzzy Plims" and a website address. There are two potted plants and a staircase leading up to the entrance.

A beach with thatched umbrellas, palm trees, and lounge chairs.

4. Breezy Palms Resort

Breezy Palms Resort

2.5 star property

Matecumbe

9.0 out of 10, Wonderful, (762 reviews)

9.0/10

Wonderful

(762 reviews)

"Such a great place to stay!!"

Gavin

$129 nightly

The price is $145

$145 total

Oct 21 - Oct 22

Total with taxes and fees

Breezy Palms Resort

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

A beach with wooden lounge chairs, palm trees, and a clear view of the ocean.

A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.

A beachfront property with a white building, a balcony with a white railing, and palm trees.

5. La Jolla Resort

La Jolla Resort

2.5 star property

Matecumbe

9.2 out of 10, Wonderful, (1,006 reviews)

9.2/10

Wonderful

(1,006 reviews)

"Nice hotel."

Brett

$131 nightly

The price is $147

$147 total

Oct 13 - Oct 14

Total with taxes and fees

La Jolla Resort

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

A tropical resort with a swimming pool, palm trees, and a waterfall.

A hotel room with a large bed, a television, a dining area with chairs, a table, and a view of the ocean.

A bar area with a thatched roof, wooden chairs, and a view of the ocean.

6. Cheeca Lodge & Spa

Cheeca Lodge & Spa

5.0 star property

Matecumbe

9.2 out of 10, Wonderful, (1,471 reviews)

9.2/10

Wonderful

(1,471 reviews)

"Staff is very helpful, rooms are clean, and there is a lot to do on the property!"

Morgan

$226 nightly

The price is $254

$254 total

Oct 13 - Oct 14

Total with taxes and fees

Cheeca Lodge & Spa

A balcony with a view of a beach, a pool, and a thatched-roof structure.

An aerial view of a marina with docked boats, a building with balconies, and a beach area.

A pool area with lounge chairs and umbrellas, surrounded by palm trees and buildings.

A beach scene with two yellow beach chairs and a person lying on one.

7. Hadley Resort and Marina

Hadley Resort and Marina

3.5 star property

Matecumbe

7.6 out of 10, Good, (1,000 reviews)

7.6/10

Good

(1,000 reviews)

"Great place"

weder

$188 nightly

The price is $212

$212 total

Nov 9 - Nov 10

Total with taxes and fees

Hadley Resort and Marina

A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

A row of colorful beach huts with palm trees in the background.

A beach with colorful buildings, kayaks, and lounge chairs.

A beach resort with palm trees, a thatched hut, and a purple building with a window.

8. La Siesta Resort & Villas

La Siesta Resort & Villas

4.0 star property

Matecumbe

8.6 out of 10, Excellent, (1,000 reviews)

8.6/10

Excellent

(1,000 reviews)

"Great place to stay!"

Brianne

$252 nightly

The price is $283

$283 total

Nov 8 - Nov 9

Total with taxes and fees

La Siesta Resort & Villas

A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

A coastal resort with a marina, clear blue water, and lush greenery.

A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

A beach with palm trees, a wooden pier, and beach chairs.

9. Pines & Palms Resort

Pines & Palms Resort

3.0 star property

Matecumbe

9.2 out of 10, Wonderful, (1,001 reviews)

9.2/10

Wonderful

(1,001 reviews)

"It was a great time staying at the resort. Really enjoyed that they had a bartender at the pool in the evenings."

Colt

$278 nightly

The price is $313

$313 total

Oct 15 - Oct 16

Total with taxes and fees

Pines & Palms Resort

A beachside lounge with a wooden deck, thatched roof, and tropical plants.

A resort with a central swimming pool surrounded by palm trees and a view of the ocean.

A waterfront property with a paved walkway, palm trees, and a white building with a dock.

A bar area with a counter, stools, and potted plants.

10. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 star property

Matecumbe

9.0 out of 10, Wonderful, (466 reviews)

9.0/10

Wonderful

(466 reviews)

"Nice place very clean , quiet . Was great stay for us , thank you"

beata

$353 nightly

The price is $397

$397 total

Oct 18 - Oct 19

Total with taxes and fees

Bayside Villas by Islander Resort

A balcony with a wooden table, two chairs, and a view of the ocean and palm trees.

A beachside patio with a thatched roof, two lounge chairs, and a view of the ocean.

A pool area with clear blue water, white lounge chairs, and palm trees.

A gated entrance to a resort with palm trees and a clear sky.

11. The Islands of Islamorada

The Islands of Islamorada

5.0 star property

Matecumbe

9.6 out of 10, Exceptional, (81 reviews)

9.6/10

Exceptional

(81 reviews)

"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"

Christian

$564 nightly

The price is $633

$633 total

Oct 14 - Oct 15

Total with taxes and fees

The Islands of Islamorada

A beachside lounge area with sun loungers, a thatched structure, and a view of the ocean.

A two-story building with a balcony, surrounded by palm trees and a sandy ground.

A beach with an American flag, palm trees, and a barbecue area.

A spacious living area with a round dining table, a sofa, and a TV mounted on the wall.

12. Sands of Islamorada

Sands of Islamorada

2.5 star property

Matecumbe

8.8 out of 10, Excellent, (416 reviews)

8.8/10

Excellent

(416 reviews)

"Very small, Was quiet and relaxing."

Nicolas

$204 nightly

The price is $230

$230 total

Oct 12 - Oct 13

Total with taxes and fees

Sands of Islamorada

An indoor wooden structure with a thatched roof, multiple hanging spherical lights, and a central seating area.

A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

A hotel room with a large bed, a nightstand, a lamp, a window with curtains, and a view of greenery outside.

13. Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

Matecumbe

$3,426 nightly

The price is $3,801

$3,801 total

Oct 17 - Oct 18

Total with taxes and fees

Private Island Suite w/ Terrace & Balcony @Islamorada - Coconut Palm Suite

A kitchen area with white cabinets, a green countertop, and various kitchen items.

A balcony with a view of greenery and a river. There are two wicker chairs with cushions.

14. Charming Suite @Islamorada With Pool Access - Twilight Suite

Charming Suite @Islamorada With Pool Access - Twilight Suite

Matecumbe

$2,284 nightly

The price is $2,534

$2,534 total

Oct 17 - Oct 18

Total with taxes and fees

Charming Suite @Islamorada With Pool Access - Twilight Suite

A covered outdoor area with a white railing, a table with a straw hat, and a bench.

15. Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

Matecumbe

$1,860 nightly

The price is $2,064

$2,064 total

Oct 17 - Oct 18

Total with taxes and fees

Terrace & Florida Bay View Suite @Islamorada - Shangri La Suite

A pool with a view of a bridge and umbrellas in the background.

16. Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

Matecumbe

$1,849 nightly

The price is $2,051

$2,051 total

Oct 17 - Oct 18

Total with taxes and fees

Oceanfront Manatee Suite w/ Private Patio @Islamorada - Manatee Suite

17. Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

Matecumbe

$1,713 nightly

The price is $1,901

$1,901 total

Oct 17 - Oct 18

Total with taxes and fees

Serene Moon Suite w/ Jacuzzi + Garden View @Islamorada- Moon Suite

A pathway through a landscaped garden with various plants and a building in the background.

18. Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

Matecumbe

$1,142 nightly

The price is $1,267

$1,267 total

Oct 17 - Oct 18

Total with taxes and fees

Peaceful Garden King Suite – Islamorada Gem - Gumbo Limbo Suite

A view from a window overlooking a beach with palm trees and a wooden pier.

An aerial view of a resort with a swimming pool, lounge chairs, and palm trees.

19. Casa Morada

Casa Morada

3.5 star property

Matecumbe

9.4 out of 10, Exceptional, (462 reviews)

9.4/10

Exceptional

(462 reviews)

"Very helpful staff and great location"

David

$188 nightly

The price is $211

$211 total

Oct 28 - Oct 29

Total with taxes and fees

Casa Morada

20. Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana Suite

Matecumbe

$2,282 nightly

The price is $2,532

$2,532 total

Oct 17 - Oct 18

Total with taxes and fees

Jacuzzi Suite Overlooking the Sea @Islamorada - Iguana 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