House
10.0(193 Reviews)
2 Bedrooms
6 Guests
Oceanfront
Parking
Pool
Ocean View
US $445/Night
7 Nights - US $3,113
Upper Matecumbe Key Villa Rentals
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Compare Villas, Resorts, & Rentals in Upper Matecumbe Key
10.0
House
10.0(2 Reviews)
3 Bedrooms
6 Guests
Breakfast- Parking
- Pool
Spa
US $966/Night
7 Nights - US $6,762
US $185/Night
7 Nights - US $1,293
House
10.0(193 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $361/Night
7 Nights - US $2,527
US $2,500/Night
7 Nights - US $17,500
House
10.0(152 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $353/Night
7 Nights - US $2,473
Cottage
10.0(141 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
Balcony/Terrace
View
US $358/Night
7 Nights - US $2,509
Villa
10.0(126 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $442/Night
7 Nights - US $3,096
House
10.0(103 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
Hot Tub- Parking
- Pool
US $772/Night
7 Nights - US $5,403
Luxury Places to Stay in Upper Matecumbe Key
Over 1434+ Luxury Places to Stay in or Near Upper Matecumbe Key
House
10.0(2 Reviews)
7 Bedrooms
14 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
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Villa
1 Bedroom
14 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $7,936/Night
7 Nights - US $55,552
Villa
10.0(1 Review)
10 Bedrooms
22 Guests
Private Pool- Oceanfront
- Breakfast
- Parking
US $3,657/Night
7 Nights - US $25,599
House
9.0(2 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
US $3,582/Night
7 Nights - US $25,072
US $3,009/Night
7 Nights - US $21,063
House
10.0(1 Review)
8 Bedrooms
22 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $3,000/Night
7 Nights - US $20,999
Hotel
- Parking
- Pool
- Balcony/Terrace
Kitchen
US $2,836/Night
7 Nights - US $19,850
House
10.0(3 Reviews)
6 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $2,815/Night
7 Nights - US $19,704
Top-Rated Villas with a Pool in Upper Matecumbe Key
Over 1050+ Top-Rated Private Villas with a Pool in or Near Upper Matecumbe Key
US $639/Night
7 Nights - US $4,473
House
10.0(132 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,308/Night
7 Nights - US $9,154
House
10.0(124 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $838/Night
7 Nights - US $5,865
House
10.0(119 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $1,788/Night
7 Nights - US $12,515
House
10.0(106 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $781/Night
7 Nights - US $5,468
House
10.0(95 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $502/Night
7 Nights - US $3,515
House
10.0(91 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $539/Night
7 Nights - US $3,771
House
10.0(90 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $387/Night
7 Nights - US $2,711
House
10.0(81 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $2,261/Night
7 Nights - US $15,826
Pet-Friendly Villas in Upper Matecumbe Key
Over 476+ Pet-Friendly Private Villas in or Near Upper Matecumbe Key
Villa
10.0(95 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $350/Night
7 Nights - US $2,450
House
9.5(2 Reviews)
3 Bedrooms
7 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $764/Night
7 Nights - US $5,348
House
1 Bedroom
Pet Friendly
Child Friendly
Barbecue/Outdoor Cooking
US $2,526/Night
7 Nights - US $17,685
Cottage
10.0(19 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $930/Night
7 Nights - US $6,508
Resort
9.0(1293 Reviews)
58 Guests
Private Beach- Oceanfront
EV Charge Station- Parking
US $659/Night
7 Nights - US $4,611
Cottage
10.0(16 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $627/Night
7 Nights - US $4,392
Villa
10.0(16 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $611/Night
7 Nights - US $4,274
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $249/Night
7 Nights - US $1,745
US $220/Night
7 Nights - US $1,537
Large Private Villas in Upper Matecumbe Key
Over 280+ Large Villas in or Near Upper Matecumbe Key for Groups and Families
Villa
10.0(23 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $548/Night
7 Nights - US $3,835
Villa
9.5(2 Reviews)
2 Bedrooms
6 Guests
- Private Beach
- Oceanfront
- Parking
- Pool
US $495/Night
7 Nights - US $3,465
US $1,680/Night
7 Nights - US $11,761
Villa
10.0(2 Reviews)
1 Bedroom
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $445/Night
7 Nights - US $3,118
House
8.0(3 Reviews)
5 Bedrooms
12 Guests
- Private Beach
- Oceanfront
- Parking
- Pool
US $180/Night
7 Nights - US $1,260
Villa
10.0(1 Review)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $511/Night
7 Nights - US $3,576
Villa
9.8(118 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $272/Night
7 Nights - US $1,902
US $364/Night
7 Nights - US $2,546
Villa
9.8(8 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $323/Night
7 Nights - US $2,258
Wheelchair Accessible Holiday Homes in Upper Matecumbe Key
Over 448+ Wheelchair Accessible Villas and Holiday Homes in or Near Upper Matecumbe Key
Condo
10.0(62 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $508/Night
7 Nights - US $3,555
Resort
8.6(168 Reviews)
30 Guests
- Private Beach
- Oceanfront
- Parking
- Pool
US $452/Night
7 Nights - US $3,164
US $626/Night
7 Nights - US $4,384
Condo
10.0(62 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $253/Night
7 Nights - US $1,774
Resort
8.5(768 Reviews)
75 Guests
- Private Beach
- Oceanfront
- Breakfast
- Parking
US $332/Night
7 Nights - US $2,326
Condo
10.0(34 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $388/Night
7 Nights - US $2,714
Condo
10.0(32 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $451/Night
7 Nights - US $3,160
Condo
10.0(6 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $217/Night
7 Nights - US $1,520
Condo
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $180/Night
7 Nights - US $1,261
Upper Matecumbe Key Villas, Airbnb and Holiday Homes Under $200
Over 109+ Upper Matecumbe Key Private Villas, Airbnb and Holiday Homes Under $200
House
10.0(4 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $103/Night
7 Nights - US $724
Apartment
9.5(9 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $189/Night
7 Nights - US $1,324
US $119/Night
7 Nights - US $835
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $185/Night
7 Nights - US $1,298
US $177/Night
7 Nights - US $1,242
Condo
10.0(3 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $149/Night
7 Nights - US $1,044
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $115/Night
7 Nights - US $808
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $180/Night
7 Nights - US $1,261
Condo
10.0(2 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $148/Night
7 Nights - US $1,036
Instantly Bookable Villa Rentals in Upper Matecumbe Key
Over 821+ Instantly Bookable Private Villas in or Near Upper Matecumbe Key
House
10.0(72 Reviews)
2 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $371/Night
7 Nights - US $2,598
House
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $731/Night
7 Nights - US $5,119
House
10.0(61 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $440/Night
7 Nights - US $3,083
House
10.0(59 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $496/Night
7 Nights - US $3,470
House
10.0(50 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $432/Night
7 Nights - US $3,021
Apartment
10.0(49 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $400/Night
7 Nights - US $2,800
House
10.0(40 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $387/Night
7 Nights - US $2,706
Apartment
10.0(36 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $384/Night
7 Nights - US $2,691
House
10.0(26 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $411/Night
7 Nights - US $2,878
Book a Last Minute Place to Stay in Upper Matecumbe Key
About Upper Matecumbe Key Vacation Rentals
There are more than 1443 incredible getaway rentals that are available in Upper Matecumbe Key. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Upper Matecumbe Key.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Upper Matecumbe Key, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Upper Matecumbe Key. Places to stay near Upper Matecumbe Key are 677.88 ft² on average, with prices averaging US $784 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Upper Matecumbe Key. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Upper Matecumbe Key, FL
There are 203 hotels in Upper Matecumbe Key 58 resorts, and 1016 rentals
- Prices for a holiday home in Upper Matecumbe Key start at US $103
- Top rated vacation home in Upper Matecumbe Key is Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Most popular short term in Upper Matecumbe Key is Chesapeake Beach Resort
- Cheapest place to stay in Upper Matecumbe Key is Pool, Beach and Tennis Court! Fishing, swimming and relaxation!
- Most expensive holiday rental in Upper Matecumbe Key is Chateau On The Ocean - The Southernmost Shangrila
Recently Booked Hotels, Resorts, or Rentals in Upper Matecumbe Key
Frequently Asked Questions About Upper Matecumbe Key?
What are the top hotels or resorts in Upper Matecumbe Key?
We provide an array of great vacation destinations in Upper Matecumbe Key. If you are looking to stay in or around the Upper Matecumbe Key area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Upper Matecumbe Key:
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- OCEANSIDE ANGLERS REEF HOME- Gated community- Pool, Dock, Private Beach
- The Caribbean Resort
- Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- 5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
- 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
- Beautiful Ocean View in Angler's Reef with View of Sand Bar/Boat slip
How many vacation rentals have private pools in Upper Matecumbe Key?
We have 191 luxury villas and vacation rentals featuriung a private pool in and near Upper Matecumbe Key. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel or resort in Upper Matecumbe Key is best for families?
Searching for a family-friendly getaway in Upper Matecumbe Key? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Upper Matecumbe Key?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 1443 in the Upper Matecumbe Key area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Upper Matecumbe Key.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Coral Cove Rental Villas and Private Getaways in Florida | 643 |
