Upper Matecumbe Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Upper Matecumbe Key

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (543)
"Spacious rooms and location was great for what we needed. "
The price is ￥11,152
￥20,190 total
includes taxes & fees
Oct 13 - Oct 14
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is ￥81,109
￥99,377 total
includes taxes & fees
Oct 6 - Oct 7
The Islands of Islamorada
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
Outdoor pool, a heated pool

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (118)
"Wonderful location."
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Outdoor pool, a heated pool

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (59)
"Fabulous house! Awesome pool, fire pit, dock. My family thoroughly enjoyed every single moment here. Plenty of room for everyone. And the wild life is awesome! Manatees, tropical fish and iguanas!"
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Treasure Harbor
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

3.0 star property
8.8 out of 10, Excellent, (106)
"If you are looking for a laid back vibe with no hassle here is the place. Friendly staff. Aqualodge was cute and comfortable. Easily rented a boat for the day...found great snorkeling and beautiful views. "
The price is ￥14,598
￥37,162 total
includes taxes & fees
Oct 12 - Oct 13
Treasure Harbor
Key Largo Cottages
Boating

Key Largo Cottages

2.5 star property
9.6 out of 10, Exceptional, (24)
"Beautiful and peaceful place "
Key Largo Cottages
Island Bay Resort
Private beach, sun loungers, beach umbrellas, beach towels

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (132)
"Clean, friendly, has its own beach"
Island Bay Resort
Piece of Paradise located at Hawks Cay in Duck Key
Pool

Piece of Paradise located at Hawks Cay in Duck Key

9.6 out of 10, Exceptional, (5)
Piece of Paradise located at Hawks Cay in Duck Key
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Outdoor pool, a heated pool

Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

9.8 out of 10, Exceptional, (57)
"Great unit, nicely renovated and a good weekend! "
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Outdoor pool, a heated pool

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

9.8 out of 10, Exceptional, (224)
"We found the condo very nicely located to Key Largo, Islamorada, and Tavernier. Enjoyed restaurants with sunset bayside, snorkeling excursion off John Pennecamp state park, and the pool and tiki hut on resortPremises! Would return here if back in the area. "
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
Marina

Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

10.0 out of 10, Exceptional, (179)
"Beautiful property. Great location. We thoroughly enjoyed ourselves. "
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities
On the beach, sun loungers, beach towels

5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities

10.0 out of 10, Exceptional, (16)
"Great vacation spot , only thing missing is a good saltwater beach."
5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
Marina

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

9.8 out of 10, Exceptional, (186)
"The property was exactly as described. Great view nice amenities and friendly employees. Great location everything is close by. Already planning on coming back again "
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
VOTED BEST KEY LARGO VACATION RENTAL
Terrace/patio

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (82)
"Wonderful property! Very clean, plenty of space, and updated interior. Access to many amenities across the whole property with multiple pools, a swimming lagoon, fishing equipment, bikes, kayaks, and more. Great location to everything in Key Largo and southern Florida activities. Would highly recommend. "
VOTED BEST KEY LARGO VACATION RENTAL
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.
Smart TV, fireplace

Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.

9.6 out of 10, Exceptional, (61)
"Everything was exactly like the listing! Would definitely stay there again"
Water Front Condo in Duck Key. FREE WIFI! Overlooking the Gulf of Mexico.
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
On the beach, sun loungers, beach towels

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

9.4 out of 10, Exceptional, (98)
"Oceans views for miles! Great pool. "
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
Waterfront Tiny House w Pool, Beach, and Boat Dock
Marina

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (61)
"Excelent place "
The price is ￥16,882
￥53,334 total
includes taxes & fees
Oct 28 - Oct 29
Waterfront Tiny House w Pool, Beach, and Boat Dock
Charming Home in Key Largo
Fridge, microwave, oven, stovetop

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"Great location. Very clean very nice, stay there again"
The price is ￥9,158
￥49,476 total
includes taxes & fees
Oct 6 - Oct 7
Charming Home in Key Largo
Charming townhome with ocean views, an open porch & steps from the water
Fridge, microwave, oven, stovetop

Charming townhome with ocean views, an open porch & steps from the water

9.4 out of 10, Exceptional, (6)
"We absolutely loved the unit inside and outside! It was very clean and accommodating! Duck Key is a very beautiful area and the unit has a canal water view in the back yard! However, within a few steps you could see both the Atlantic Ocean and Golf of America with the bridge going over the water! Beautiful view from the upstairs bedroom balcony!!!! We had a couple issues, but Vacasa immediately communicated with us and had their handyman there to fix the toilet and get us a new coffee pot...
Charming townhome with ocean views, an open porch & steps from the water
Amazing Ocean view at Ocean Pointe w/Heated Pool
Terrace/patio

Amazing Ocean view at Ocean Pointe w/Heated Pool

9.6 out of 10, Exceptional, (39)
"We enjoyed our time at Ocean Point. "
Amazing Ocean view at Ocean Pointe w/Heated Pool
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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Top Upper Matecumbe Key Hotel Reviews

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"Quick in and out for business. Very Easy and simple. Check in lady was super sweet. "
Christopher 1-night trip
Posted 2 days ago
Playa Largo Resort & Spa, Autograph Collection

Find out more about Upper Matecumbe Key

Find out more about Upper Matecumbe Key

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