--- title: "Upper Matecumbe Key Holiday Rentals : Private House Rentals | No Hidden Fees - Vrbo" description: "Long stay discounts available for Upper Matecumbe Key holiday rentals. Choose from over 1,314 properties and rent an entire home in Upper Matecumbe Key with Vrbo." canonical: "https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/upper-matecumbe-key" language: en-GB market: GB currency: GBP prices_as_of: 2026-11-13T23:32:23Z --- # Upper Matecumbe Key holiday lettings ![A shark sculpture with a sign above it that reads "Islamorada Florida Keys".](https://images.trvl-media.com/place/10768/5bfec556-6f8a-4abf-b52b-cefbcbaaad50.jpg?impolicy=resizecrop&rw=1920&ra=fit&ch=480) We found 1,314 holiday rentals — enter your dates for availability ## Find spaces that suit your style [Search for Houses](https://www.vrbo.com/search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=house) House [Search for Condos/Apartments](https://www.vrbo.com/search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=apartment%5For%5Fcondo) Condo/Apartment [search for cabins](https://www.vrbo.com/search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=cabin) Cabin [search for cottages](https://www.vrbo.com/search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=cottage) Cottage [search for villas](https://www.vrbo.com/search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=villa) Villa [search for chalets](https://www.vrbo.com/search?destination=Upper+Matecumbe+Key%2C+Florida%2C+United+States+of+America®ionId=553248635975749648&latLong=24.919028%2C-80.634088&adults=2&startDate=2026-11-27&d1=2026-11-27&endDate=2026-11-29&d2=2026-11-29&property%5Ftype%5Fgroup=chalet) Chalet ## Find properties near top attractions in Upper Matecumbe Key ![A marina with boats docked, a motel, and a cafe.](https://images.trvl-media.com/place/6069243/da13ffdf-ddd2-4c35-bedc-c5b570b047e9.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium) 1 ###### [Bud n' Mary's Dive Center](https://www.vrbo.com/en-gb/search?regionId=6069243&startDate=&endDate=&locale=en%5FGB&rfrrid=slp) ![A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium) 2 ###### [Florida Keys Brewing Co.](https://www.vrbo.com/en-gb/search?regionId=553248635997958830&startDate=&endDate=&locale=en%5FGB&rfrrid=slp) ![A building with a blue facade, a large mural of a diving scene, and a statue of a diver.](https://images.trvl-media.com/place/6069257/2fd3877d-0c73-4409-9263-a837206a6b6d.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium) 3 ###### [History of Diving Museum](https://www.vrbo.com/en-gb/search?regionId=6069257&startDate=&endDate=&locale=en%5FGB&rfrrid=slp) ![A stone monument with a relief sculpture, surrounded by palm trees and a clear blue sky.](https://images.trvl-media.com/place/6063543/85e7df32-7434-48b7-aec9-bd47c62ec463.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium) 4 ###### [Hurricane Monument](https://www.vrbo.com/en-gb/search?regionId=6063543&startDate=&endDate=&locale=en%5FGB&rfrrid=slp) ![A church sign with the name Matecumbe United Methodist Church, listing Sunday School and Worship Service times.](https://images.trvl-media.com/place/553248621532652347/4e16d0f0-6625-4d57-9e35-b8a011badc77.jpg?impolicy=fcrop&w=600&h=400&p=1&q=medium) 5 ###### [Matecumbe United Methodist Church](https://www.vrbo.com/en-gb/search?regionId=553248621532652347&startDate=&endDate=&locale=en%5FGB&rfrrid=slp) ## Find the best place to stay - Upper Matecumbe Key ### [1\. 9 Million Dollar 2.5 Acre Bayside Beach Compound w Boat Dockage is One of A Kind](https://www.vrbo.com/en-gb/p2371284vb?containsVideo=false) ![Image of 9 Million Dollar 2.5 Acre Bayside Beach Compound w Boat Dockage is One of A Kind](https://media.vrbo.com/lodging/70000000/69370000/69366100/69366079/9757cf8b.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 10/10 (Exceptional, 41 reviews) Sleeps 14 · 5 bedrooms · 5+ bathrooms ### [2\. Luxury 6 bedroom - truly spectacular beachfront property](https://www.vrbo.com/en-gb/p3363008vb?containsVideo=false) ![Image of Luxury 6 bedroom - truly spectacular beachfront property](https://media.vrbo.com/lodging/94000000/93040000/93033100/93033059/cb49faaa.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 10/10 (Exceptional, 3 reviews) Sleeps 12 · 6 bedrooms · 5 bathrooms ### [3\. Islamorada Paradise - Canal Front & Private Beach Access](https://www.vrbo.com/en-gb/p1476187vb?containsVideo=false) ![Image of Islamorada Paradise - Canal Front & Private Beach Access](https://media.vrbo.com/lodging/35000000/34350000/34340500/34340409/b98e9442.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 9.6/10 (Exceptional, 22 reviews) Sleeps 6 · 4 bedrooms · 2 bathrooms ### [4\. 10 Million Dollar 2 Acre Bayside Beach Compound w Boat Dockage is One of A Kind](https://www.vrbo.com/en-gb/p2367942vb?containsVideo=false) ![Image of 10 Million Dollar 2 Acre Bayside Beach Compound w Boat Dockage is One of A Kind](https://media.vrbo.com/lodging/70000000/69340000/69338700/69338691/90e8a697.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 10/10 (Exceptional, 73 reviews) Sleeps 20 · 6 bedrooms · 6 bathrooms ### [5\. Treasure Harbor](https://www.vrbo.com/en-gb/pdp/lo/91743042?containsVideo=false) ![Image of Treasure Harbor](https://media.vrbo.com/lodging/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 9/10 (Wonderful, 185 reviews) Sleeps 6 · 2 bedrooms ### [6\. Islamorada Oceanfront Estate · Private Beach, Heated Pool & Dock](https://www.vrbo.com/en-gb/p4742203vb?containsVideo=false) ![Image of Islamorada Oceanfront Estate · Private Beach, Heated Pool & Dock](https://media.vrbo.com/lodging/120000000/119450000/119446900/119446807/cad7b410.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 10/10 (Exceptional, 4 reviews) Sleeps 12 · 5 bedrooms · 4 bathrooms ## Top rated rentals - Upper Matecumbe Key ### [Island Bay Resort](https://www.vrbo.com/en-gb/pdp/lo/13279636?containsVideo=false) ![Image of Island Bay Resort](https://media.vrbo.com/lodging/14000000/13280000/13279700/13279636/0514aa55.jpg?impolicy=resizecrop&ra=fit&rw=455&rh=455) - Guest rating: 10/10 (Exceptional, 190 reviews) - Review: Island Bay…. accommodation must for Key Largo. Cannot recommend Island Bay highly enough! Absolutely everything there that you could possibly need….. spotlessly clean , both accommodation and communal areas! Sue & Steve are a wonderful couple….. nothing was too much trouble. Only wish we had stayed longer!, by Beverley, Stayed Apr 2025 ### Peace of mind Our Book with Confidence Guarantee gives you 24/7 support ### More quality time From booking to staying, the whole process is simple and enjoyable ### All the privacy of home Enjoy full kitchens, pools, gardens and more ### More for less More space, more privacy, more amenities — more value ## Frequently Asked Questions ### What is the most popular type of holiday rental accommodation in Upper Matecumbe Key? Houses are the most popular kind of holiday rental in Upper Matecumbe Key, according to our data. Even if you have a different idea about what you want, Vrbo has properties in a variety of shapes and sizes. Compare our options to find your perfect pad. ### How much does it cost to rent a holiday rental in Upper Matecumbe Key? Different things can influence what you'll pay for your holiday rental in Upper Matecumbe Key, such as the season, length of stay and type of property. However, all Vrbo homes have one thing in common — excellent value. Simply enter your travel dates to find your ideal match. ### How much does it cost to rent a beach house in Upper Matecumbe Key? The average price for a holiday rental by the beach in Upper Matecumbe Key depends on when you'll be there and the type and size of property you're looking for. You can easily find prices on Vrbo by entering your preferred travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities that you prefer, such as WiFi, a pool and air conditioning. ### What are popular rental amenities in Upper Matecumbe Key? A fridge, a stovetop and a microwave oven head the list of most popular rental amenities in Upper Matecumbe Key. Whether you're heading away alone, with your better half or as a family group, Vrbo will help you find a holiday rental that fits your style with a load of extras you'll love. ### Are there large group holiday rentals in Upper Matecumbe Key? With 10 properties that can sleep 10 guests or more in Upper Matecumbe Key, there's no need to keep anyone off the invite list. From fun family get-togethers to special events like anniversary parties and weddings, Vrbo can help you find a large group rental to suit the occasion. ### Can I find two-bedroom holiday rentals in Upper Matecumbe Key? Upper Matecumbe Key has 22 two-bedroom holiday rentals for you to pick from. Find a holiday home with all the space and comfort you're looking for at a price that won't break the bank on Vrbo. ### Are there holiday rentals with WiFi in Upper Matecumbe Key? Whether you want to stay in touch with world events, write a few emails or surf your social networks, there are 28 holiday homes with WiFi in Upper Matecumbe Key. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday. ### How old do you have to be to rent a holiday rental in Upper Matecumbe Key? The minimum age is usually 16, 18 or 21\. It can differ from property to property on Vrbo, so check the rules of your preferred Upper Matecumbe Key holiday home before making a booking. ### How long can I rent a holiday rental in Upper Matecumbe Key for? How long you can rent a holiday rental in Upper Matecumbe Key differs according to the property. Simply enter your preferred travel dates to view a list of options offering extended stays. With a range of features like laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover someplace just right to call your home away from home in Upper Matecumbe Key. ## More holiday ideas - [Lodging](?equalTargetTab=tab-0) - [Holiday Rentals](?equalTargetTab=tab-1) - [Apartments in Marathon](https://www.vrbo.com/en-gb/holiday-rentals/apartments/united-states/florida/monroe-county/marathon) - [Beach rentals in Marathon](https://www.vrbo.com/en-gb/holiday-rentals/beach/united-states/florida/monroe-county/marathon) - [Rv and caravan rentals in Marathon](https://www.vrbo.com/en-gb/holiday-rentals/caravans/united-states/florida/monroe-county/marathon) - [Cottages in Marathon](https://www.vrbo.com/en-gb/holiday-rentals/cottages/united-states/florida/monroe-county/marathon) - [Houseboats in Marathon](https://www.vrbo.com/en-gb/holiday-rentals/houseboats/united-states/florida/monroe-county/marathon) - [Houses in Marathon](https://www.vrbo.com/en-gb/holiday-rentals/houses/united-states/florida/monroe-county/marathon) - 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[Houses in Key Largo](https://www.vrbo.com/en-gb/holiday-rentals/houses/united-states/florida/monroe-county/key-largo) - [Cabins in Key Largo](https://www.vrbo.com/en-gb/holiday-rentals/log-cabins/united-states/florida/monroe-county/key-largo) - [Oceanfront rentals in Key Largo](https://www.vrbo.com/en-gb/holiday-rentals/oceanfront/united-states/florida/monroe-county/key-largo) - [Rentals with pool in Key Largo](https://www.vrbo.com/en-gb/holiday-rentals/pools/united-states/florida/monroe-county/key-largo) - [Resorts in Key Largo](https://www.vrbo.com/en-gb/holiday-rentals/resorts/united-states/florida/monroe-county/key-largo) - [Townhouses in Key Largo](https://www.vrbo.com/en-gb/holiday-rentals/townhouses/united-states/florida/monroe-county/key-largo) - [Villas in Key Largo](https://www.vrbo.com/en-gb/holiday-rentals/villas/united-states/florida/monroe-county/key-largo) - [Longstay Hotels in Key Largo](https://www.vrbo.com/en-gb/tgp/lodging/theme/longstay/8369/key-largo) - [Lower Matecumbe Key Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/lower-matecumbe-key) - [Theater of the Sea Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/theater-of-the-sea-on-islamorada) - [Coral Cove Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/coral-cove) - [Sea Gull Condos Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/sea-gull-condos) - [Windley Key Fossil Reef Geological State Park Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/windley-key-fossil-reef-geological-state-park) - [Islamorada Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada) - [Seabreeze Trailer Park Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/seabreeze-trailer-park) - [Panhandle Key Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/panhandle-key) - [Plantation Key Colony Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/plantation-key-colony) - [Coral Harbour Club Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/coral-harbour-club) - [Bay Harbour Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/bay-harbour) - [Windley Key Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/windley-key) - [Plantation by the Sea Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-by-the-sea) - [Lower Matecumbe Beach Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/lower-matecumbe-beach) - [Islamorada County Park Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/islamorada-county-park) - [History of Diving Museum Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/history-of-diving-museum) - [Futura Yacht Club Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/futura-yacht-club) - [White Marlin Beach Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/white-marlin-beach) - [Indian Waterways Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/indian-waterways) - [Summer Sea Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/summer-sea) - [Plantation Key Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key) - [Holiday House Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/holiday-house) - [Founders Park Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/founders-park) - [Ocean Harbour Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/ocean-harbour) - [Sunset Drive Beach Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/lower-matecumbe-beach/sunset-drive-beach) - [Port Antigua Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/port-antigua) - [Executive Bay Club Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/plantation-key/executive-bay-club) - [Sunshine Estates Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/sunshine-estates) - [Anglers Reef Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/anglers-reef) - [Venetian Shores Holiday Rentals](https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/islamorada/venetian-shores) ## Other language versions ```yaml hreflang: x-default: https://www.vrbo.com/vacation-rentals/usa/florida/keys/islamorada-area/upper-matecumbe-key en-CA: https://www.vrbo.com/en-ca/vacation-rentals/united-states/florida/monroe-county/upper-matecumbe-key sv-SE: https://www.vrbo.com/sv-se/semesterbostad/usa/florida/monroe-county/upper-matecumbe-key fi-FI: https://www.vrbo.com/fi-fi/loma-assunto/yhdysvallat/florida/monroe-county/upper-matecumbe-key fr-CA: https://www.vrbo.com/fr-ca/location-vacances/%C3%A9tats-unis-dam%C3%A9rique/floride/comt%C3%A9-de-monroe/upper-matecumbe-key de: https://www.fewo-direkt.de/d/311706/upper-matecumbe-key it-IT: https://www.vrbo.com/it-it/case-vacanze/stati-uniti-damerica/florida/contea-di-monroe/upper-matecumbe-key el-GR: https://www.vrbo.com/el-gr/%CE%B4%CE%B9%CE%B1%CE%BC%CE%BF%CE%BD%CE%AE-%CE%B4%CE%B9%CE%B1%CE%BA%CE%BF%CF%80%CF%8E%CE%BD/%CE%B7%CE%BD%CF%89%CE%BC%CE%AD%CE%BD%CE%B5%CF%82-%CF%80%CE%BF%CE%BB%CE%B9%CF%84%CE%B5%CE%AF%CE%B5%CF%82/%CF%86%CE%BB%CF%8C%CF%81%CE%B9%CE%BD%CF%84%CE%B1/monroe-county/upper-matecumbe-key de-AT: https://www.vrbo.com/de-at/urlaubsunterkunft/vereinigte-staaten/florida/monroe-county/upper-matecumbe-key da-DK: https://www.vrbo.com/da-dk/ferieboliger/usa/florida/monroe-county/upper-matecumbe-key fr: https://www.abritel.fr/d/311706/upper-matecumbe-key en-SG: https://www.vrbo.com/en-sg/holiday-accommodation/united-states/florida/monroe-county/upper-matecumbe-key en-AU: https://www.stayz.com.au/d/311706/upper-matecumbe-key en-GB: https://www.vrbo.com/en-gb/holiday-rentals/united-states/florida/monroe-county/upper-matecumbe-key nl-NL: https://www.vrbo.com/nl-nl/vakantiehuizen/verenigde-staten/florida/monroe-county/upper-matecumbe-key ja-JP: https://www.vrbo.com/ja-jp/%E5%AE%BF%E6%B3%8A/%E3%82%A2%E3%83%A1%E3%83%AA%E3%82%AB/%E3%83%95%E3%83%AD%E3%83%AA%E3%83%80%E5%B7%9E/monroe-county/upper-matecumbe-key pt-PT: https://www.vrbo.com/pt-pt/alojamento-de-f%C3%A9rias/estados-unidos/florida/monroe-county/upper-matecumbe-key es-ES: https://www.vrbo.com/es-es/alquiler-vacacional/estados-unidos/florida/condado-de-monroe/upper-matecumbe-key pt-BR: https://www.vrbo.com/pt-br/alugue-temporada/estados-unidos/fl%C3%B3rida/monroe-county/upper-matecumbe-key en-NZ: https://www.bookabach.co.nz/d/311706/upper-matecumbe-key no-NO: https://www.vrbo.com/no-no/overnatting/usa/florida/monroe-county/upper-matecumbe-key en-US: https://www.vrbo.com/vacation-rentals/usa/florida/keys/islamorada-area/upper-matecumbe-key ```