Search Vacation Homes in Upper Matecumbe Key

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Vacation Homes in Upper Matecumbe Key

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

9.4 out of 10, Exceptional, (66)
"Great tiny house, enjoyed our stay"
The price is ¥21,039
¥58,543 total
includes taxes & fees
Jun 23 - Jun 24
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

9.6 out of 10, Exceptional, (31)
"Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. "
The price is ¥12,371
¥41,921 total
includes taxes & fees
Jun 23 - Jun 24
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (55)
"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "
The price is ¥23,395
¥61,775 total
includes taxes & fees
Jun 30 - Jul 1
Waterfront Tiny House w Pool, Beach, and Boat Dock

Waterfront Pool, Beach, Dock, Kayaks, Paddleboards

9.8 out of 10, Exceptional, (75)
"Loved our stay!"
The price is ¥27,163
¥66,158 total
includes taxes & fees
Jun 23 - Jun 24
Waterfront Pool, Beach, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (112)
"Best sunrise site."
The price is ¥30,617
¥70,335 total
includes taxes & fees
Jul 8 - Jul 9
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

The Grand Lodge Right On The Water at Largo Resort by Rentyl Resorts

9.6 out of 10, Exceptional, (4)
"would stay again"
The price is ¥139,274
¥182,561 total
includes taxes & fees
Jul 6 - Jul 7
The Grand Lodge Right On The Water at Largo Resort by Rentyl Resorts

Enchanted Paradise Bungalow at Largo Resort

2.0 star property
The price is ¥62,659
¥85,466 total
includes taxes & fees
Jun 27 - Jun 28
Enchanted Paradise Bungalow at Largo Resort

Sunrise Bungalow w/Plenty of Shade at Largo Resort by Rentyl Resorts

2.0 star property
The price is ¥60,175
¥82,923 total
includes taxes & fees
Jun 29 - Jun 30
Sunrise Bungalow w/Plenty of Shade at Largo Resort by Rentyl Resorts

The Largo Airstream in Paradise at Largo Resort by Rentyl Resorts

The price is ¥46,376
¥64,967 total
includes taxes & fees
Jun 27 - Jun 28
The Largo Airstream in Paradise at Largo Resort by Rentyl Resorts

Tranquil Bungalow at the Beautiful at Largo Resort by Rentyl Resorts

9.6 out of 10, Exceptional, (7)
"10/10! This property itself is secluded and very safe. The pool and views were breathtaking. The complimentary paddle boards and bicycles were fun and just an extra service that bettered our experience. The employees were amazing, kind, and professional. The bungalow was so comfortable and smelt amazing when we entered. Beds were comfortable and the little kitchen was used! Plates, silverwear, & cups were provided thankfully. The host!!!! 100/10. Thank you!!!! She was able to provide a nice...
The price is ¥62,495
¥85,243 total
includes taxes & fees
Jun 27 - Jun 28
Tranquil Bungalow at the Beautiful at Largo Resort by Rentyl Resorts

Tropical House By The Shore at Largo Resort by Rentyl Resorts

The price is ¥81,267
¥109,308 total
includes taxes & fees
Jun 30 - Jul 1
Tropical House By The Shore at Largo Resort by Rentyl Resorts

Lovely Bungalow w/ Plenty Of Shade at Largo Resort by Rentyl Resorts

10.0 out of 10, Exceptional, (17)
"Our bungalow was very clean and the beds were very comfortable! It was almost like we we're on our own private island and my 8 year old loved it! We hope to come back on our next visit!"
The price is ¥60,333
¥82,413 total
includes taxes & fees
Jun 27 - Jun 28
Lovely Bungalow w/ Plenty Of Shade at Largo Resort by Rentyl Resorts

Serene Bungalow in Paradise at Largo Resort by Rentyl Resorts

10.0 out of 10, Exceptional, (2)
"Really enjoyed the condo, loved the kayaks and SPBs, the pool and the view from the pool at sunset were awesome! Would stay here again! Thanks"
The price is ¥62,495
¥85,243 total
includes taxes & fees
Jun 24 - Jun 25
Serene Bungalow in Paradise at Largo Resort by Rentyl Resorts

Cozy Bungalow w/ Sunset Ocean View at Largo Resort Resort by Rentyl Resorts

9.0 out of 10, Wonderful, (2)
"We got everything we need, a relaxing place, great service, easy to find, restaurants all over the place and most important of all very clean and beautiful. We loved."
The price is ¥78,735
¥105,688 total
includes taxes & fees
Jun 27 - Jun 28
Cozy Bungalow w/ Sunset Ocean View at Largo Resort Resort by Rentyl Resorts

Charming 2-bedroom RV Hideaway campground in Key Largo; Sun & Fun!

The price is ¥26,168
¥47,466 total
includes taxes & fees
Jun 23 - Jun 24
Charming 2-bedroom RV Hideaway campground in Key Largo; Sun & Fun!

Charming 2-bedroom mobile home with WiFi and AC in Key Largo

The price is ¥26,168
¥51,610 total
includes taxes & fees
Jun 24 - Jun 25
Charming 2-bedroom mobile home with WiFi and AC in Key Largo

NICE BOAT IN THE FL KEYS

6.4 out of 10, (5)
"It was great."
The price is ¥36,250
¥51,330 total
includes taxes & fees
Jun 22 - Jun 23
NICE BOAT IN THE FL KEYS

Casa Largo

9.0 out of 10, Wonderful, (125)
"The newlyweds wished they could have stayed longer."
The price is ¥44,341
¥90,554 total
includes taxes & fees
Jun 23 - Jun 24
Casa Largo

Renovated Waterfront Modern Luxury, Lagoon, Marina, Tennis, Bikes, Pickleball

10.0 out of 10, Exceptional, (56)
"Beautiful,clean, great location"
The price is ¥66,148
¥120,357 total
includes taxes & fees
Jul 2 - Jul 3
Renovated Waterfront Modern Luxury, Lagoon, Marina, Tennis, Bikes, Pickleball

Kawama L4 - Upscale Oceanside Villa with Marina

9.6 out of 10, Exceptional, (135)
"This property was perfect in the heart of key largo with pool and ocean access. Had everything we need and even included two bikes! Great stay overall!"
The price is ¥53,500
¥103,107 total
includes taxes & fees
Jul 1 - Jul 2
Kawama L4 - Upscale Oceanside Villa with Marina
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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