Upper Matecumbe Key Holiday Rentals

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Holiday Rentals in Upper Matecumbe Key

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (421)
"We visited Breezy Palms for our 20th wedding anniversary. We took advantage of the boat rental on site, had a great day on the water. Played cards on our lanai. Used the lovely pool, walked to local restaurants, and had a memorable time. Definitely will be back!"
The price is AU$360
includes taxes & fees
6 Apr - 7 Apr
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Everything was lovely except I felt rushed on my departure date. A front desk representative knocked around 9am to find out what time I was leaving. If your check out policy is 11am, you should not knock on people’s door to find out what time they are planning on leaving. It doesn’t feel like a luxurious experience when you do. In addition to the early knock, the entire housekeeping staff was waiting by my front door when I checked out at 10:25. What if I wasn’t checking out at 10:25 and was...
The price is AU$1,122
includes taxes & fees
6 Apr - 7 Apr
The Islands of Islamorada

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
Key Largo Cottages

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (48)
"Kawama villa's are located in a quiet area; with a lagoon, 2 pools, ocean/beach. We used bikes and kayaks, and enjoyed some "seniors" activities, too.. Sunsets were beautiful."
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Island Bay Resort

2.5 star property
9.8 out of 10, Exceptional, (106)
"Lovely private place! Clean in and out, friendly staff, loved every second staying here!! Would absolutely love to stay again"
Island Bay Resort

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

8.8 out of 10, Excellent, (29)
"Nice facilities. Wish we had better weather. Always enjoy our home away from home. KEYS LIFE FOR ME!!!!"
The price is AU$572
includes taxes & fees
5 Apr - 6 Apr
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

9.8 out of 10, Exceptional, (168)
"Clean, short walk to the beach or pool. Great place to stay."
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (54)
"Our stay at Barbara's tiny home was amazing! The property was phenomenally clean, and all the neighbors within the campground were very nice. 100% would stay here again on my next visit to key largo!"
The price is AU$724
includes taxes & fees
12 Apr - 13 Apr
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Welcome to Paradise!

9.6 out of 10, Exceptional, (60)
"We were there for a destination wedding. The room and property were everything we’d hoped for. Met a number of other guests and had a great time getting to know each other. Overall it was a wonderful experience and the condo was great!"
Welcome to Paradise!

ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???

7.0 out of 10, Good, (11)
"We stayed one night while passing through. Had what we needed. Quiet neighborhood, good parking, easy to find. Restaurant with live music just around the canal (or listen from the boat). Thank you for sharing your space!"
The price is AU$461
includes taxes & fees
23 Mar - 24 Mar
ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???

Capt Craig's 2 Bedroom/1 bath Apartment in Tavernier, Florida Keys

9.8 out of 10, Exceptional, (10)
"The place was clean and had most of the things that would need. The second queen bedroom did not have a TV. That was the only downfall. Even though it was above the restaurant you did not hear anything."
The price is AU$761
includes taxes & fees
8 Apr - 9 Apr
Capt Craig's 2 Bedroom/1 bath Apartment in Tavernier, Florida Keys

Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

9.6 out of 10, Exceptional, (141)
"Best equipped condo ever, also nice firm mattresses. The only little glitch, was getting the keys out of the lock box. This could be replaced! We would love to stay here again!"
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

Villa Largo Island Retreat

9.4 out of 10, Exceptional, (30)
"There were a few maintenance issues, but nothing that got in the way of my group having a great time. Owner very responsive and helpful. We would definitely stay again. "
Villa Largo Island Retreat

Relax in our little piece of paradise! LAST MINUTE SPECIAL for 3/2 TO 3/8 HURRY!

9.6 out of 10, Exceptional, (9)
"Our 3night stay was wonderful!Silvia, our host has created a beautiful outdoor lanai with everything you could want.The outdoor kitchen is a major plus!Everything was very clean, and the queen bed was very comfortable.We were very happy with this paradise!Five stars all the way!!Mimi Molden"
Relax in our little piece of paradise! LAST MINUTE SPECIAL for 3/2 TO 3/8 HURRY!

Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys

9.8 out of 10, Exceptional, (18)
"Very nice property and place to stay - VRBO did not send check in details - thankfully the owner was on property. "
The price is AU$631
includes taxes & fees
8 Apr - 9 Apr
Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys

Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

9.8 out of 10, Exceptional, (10)
"Really nice place, no surprises. Location was excellent and pictures and description very accurate. Unfortunately, the weather was not in our favor but can't control that! Would definitely stay here again."
The price is AU$674
includes taxes & fees
18 Mar - 19 Mar
Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

9.4 out of 10, Exceptional, (96)
"Pool was warm, kids loved to see the fish in the lagoon. Walked out to the ocean morning and night. Would have loved to kayak down by the ocean but there were no paddles. Walking distance to great restaurants."
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (73)
"We had a great time. The accommodations had everything we needed. We loved having access to kayaks and paddle boards. Great and safe area to walk and ride bikes. They had fire pits and a great rock peninsula area to view sunsets and sunrises. There was a marina with fishing opportunities leaving area marina. The only negatives were no working bikes and not a fourth bedroom. It really was 3 bedrooms with a den area with a couch that made a bed.Would go again! Norman, the property manager, was the...
VOTED BEST KEY LARGO VACATION RENTAL

Cozy place in Calusa Key Largo

9.4 out of 10, Exceptional, (9)
"This camper was a great value for the area. Very nice pool and campground as well "
The price is AU$540
includes taxes & fees
24 Mar - 25 Mar
Cozy place in Calusa Key Largo

Mangrove Marina and Resort Aqualodge Houseboats

3.0 star property
9.4 out of 10, Exceptional, (328)
"We stayed in the Grey Lady and it was the perfect slip! Quiet, views of the bay/mooring field/mangroves. Limited kitchen amenities if you are "eating in". All staff friendly and helpful. WiFi sketchy."
Mangrove Marina and Resort Aqualodge Houseboats
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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Other types of properties in Upper Matecumbe Key you may be interested in

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1045)
"Love Cheeca"
The price is AU$1,433
includes taxes & fees
30 Mar - 31 Mar
Cheeca Lodge & Spa

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1004)
"It would be nice to have music during the day Coffee availability would be a great idea as well Loved the property, the staff and convenience to other restaurants and shopping Highly recommend!!"
The price is AU$800
includes taxes & fees
30 Mar - 31 Mar
Islander Resort

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1208)
"Great stay great staff great spot!"
The price is AU$669
includes taxes & fees
30 Mar - 31 Mar
Amara Cay Resort
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.