Islamorada, Florida

The Oasis

3 bedrooms 4 beds 4 baths 8 guests

About the property

See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler. You will escape to the ultimate paradise at our stunning oceanside estate in the Florida Keys. Your majestic property is over 2.75 acres of landscaped beauty. The space It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler. You will escape to the ultimate paradise at our stunning oceanside estate in the Florida Keys. Your majestic property is over 2.75 acres of landscaped beauty. You will see there are over 100 palm trees, about 60 of them lit up at night, some of the tallest around, including the largest enclinada tree in the Keys! Their graceful presence puts you in Jimmy Buffett mode as the cooling Atlantic Ocean breeze blows in your hair. When you relax in the pool, the view of Alligator Reef Light on the horizon and the boats going by provide a backdrop while sipping your margaritas. You will never worry about a crowded beach. You will swim in the crystal blue water or stay on top with our kayaks and paddleboards for exercise. Consisting of 2 homes, the main home is 1 bedroom and 1.5 baths while the other home is 2 bedrooms and 1 bath, each with a fully stocked kitchen with all new stainless steel appliances and a living room with amazing ocean views for you to enjoy. Amenities include your private heated (or cooled) salt-water pool, 4 kayaks, and 2 paddleboards, among other items. Dog friendly and in the HEART of Islamorada on Upper Matecumbe, you will be less than a mile from Publix. And, of course, the homes are 100% smoke-free. ♛ Main House (2nd Floor): King-Size Tempurpedic adjustable bed ♛ Guest House (1st Floor): Queen-Size bed ♛ Guest House (1st Floor): Queen-Size and Full-Size bed ✔ Pillows, Linens, and Sheets ✔ 50" Smart TVs with Basic Cable ✔ Closets with Hangers and Shelves ✔ Dressers with Spacious Drawers ✔ Night Stands with Alarm Clock, Wireless Charger, and Reading Lamps ✔ Luggage Racks Since there are some great restaurants and bars very close for you to enjoy, you can simply bike to them if you don't want to drive and worry about parking. Proximity is key as you are in the heart of Islamorada and very close to everything you need. You have plenty of opportunities for adventure. We supply 6 high-end 5-speed beach bikes with large tires for handling patches of sand. Islamorada Brewery is .25 miles away, and Chef Michaels is less than a mile. Brizo faucets adorn all of your sinks, and hand-painted custom art adorns the walls. There are 5 50" Smart TVs with 150 channels of programming in addition to Netflix and Prime apps. Ubiquiti Enterprise-grade WiFi covers every inch of the property for flawless high-speed internet. Our professional mosquito control system has spray heads throughout the property and keeps mosquitos at bay as they spray throughout the day. ✔ Tub Shower ✔ Towels ✔ Hair Dryer While drinking coffee in your outdoor living room, focus on the water, as there is a short window when dolphins feed on baitfish and come as close as 25' to our beach! This is the best way to start the day as you watch the sunrise. Enjoying a glass of wine out here at the end of the day brings you right back to where you started. Be sure to repeat daily. ✔ Microwave ✔ Stove ✔ Oven ✔ Toaster ✔ Blender ✔ Hot Water Kettle ✔ Coffee Makers (Keurig Machine + Drip Coffee) ✔ Refrigerator/Freezer ✔ Dishwasher ✔ Glasses ✔ Silverware ✔ Pots & Pans The rare, plush green grass is a pleasure to walk on to and from the pool....a rarity in the keys. Our gated entrance keeps your stay private and secure. Did you drive your Tesla here? GREAT! We have an onsite charger for you as well. Stay here, and you will see why we boast the best views and stay around! * We supply all linens, including beach towels * 6 high-end bikes for getting around Upper Mat * 2 Paddleboards * 2 single-person kayaks * Life vests for 6 people * 2 dual-person kayaks * Bocce Ball * Cornhole * Enterprise-grade Wifi that covers the entire estate * Tesla and NEMA 50-14 EV charger * JBL portable speaker for pool tunes * Outdoor seating, chaise lounges, and rocking chairs * Fully stocked kitchen and all proper stemware for drinks * Tempurpedic Adjustable bed in the main house * A Printer/Scanner/Copier For Use * Gated for privacy and security This is a non-smoking property. There are no fences around the pool or ocean, so it is not advised for young children. Other than the already mentioned amenities, our home also comes with the following: ✔ High-Speed Wi-Fi ✔ Self Check-In (Smart Lock) ✔ Air Conditioning ✔ Heating ✔ Laundry Room (Washer/Dryer, Iron/Board, Utility Sink) June through November is hurricane season in Florida, and travel insurance is suggested during this time frame. May through September, sargassum can be plentiful on the beach, but it is a necessary part of the fishing in the Keys. Islamorada license # VR-235 ★ COVID-19 SANITIZATION ★ The Health, safety, and well-being of our guests are of the utmost importance. For this reason, we conduct a thorough cleaning process after each check-out. ★ DOG-FRIENDLY HOME ★ Bring your furry friends along for an exciting vacation. They'll enjoy and run around the patio outdoors while you relax in the pool. A $350 dog fee applies. ★ NO SMOKING ★ Please refrain from smoking inside the home or community! Any smoking evidence will result in odor removal and furniture cleaning fees. ★ NO PARTIES/EVENTS ★ ★ BOOKING ★ A signed rental agreement and a security deposit are required for booking and following Airbnb and VRBO policies. ★ OUTDOOR CAMERAS ★ Outdoor (only) security cameras are placed in the following locations: 2 Ring and 1 camera outside of the front gate entrance, 2 at the garage facing south at the driveway and east of the garage, 1 at the main house at kayaks, and 6 at the guest house facing 1 at Tesla charger, 1 at the pool, 1 at the beach, 1 at the driveway, 1 at guesthouse door, and 1 toward main house stairs. All are to mitigate trespassers when the home is empty, and they are not monitored for theft. Weddings, parties, or any such event is not permissible on the property. Guest access By code Other things to note * Private Pool * EV Charger * 200' property line, half is a sandy beach * Beach towels provided * 4 kayaks and 2 paddleboards * 6 bikes * AMAZING views from the entire property * Gated and fenced for privacy 2 homes with their own kitchens and living rooms, the main home has 1 bedroom and 1.5 bathrooms while the guest house has 2 bedrooms with 1 bathroom.

See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler. You will escape to the ultimate paradise at our stunning oceanside estate in the Florida Keys. Your majestic property is over 2.75 acres of landscaped beauty. The space It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler. You will escape to the ultimate paradise at our stunning oceanside estate in the Florida Keys. Your majestic property is over 2.75 acres of landscaped beauty. You will see there are over 100 palm trees, about 60 of them lit up at night, some of the tallest around, including the largest enclinada tree in the Keys! Their graceful presence puts you in Jimmy Buffett mode as the cooling Atlantic Ocean breeze blows in your hair. When you relax in the pool, the view of Alligator Reef Light on the horizon and the boats going by provide a backdrop while sipping your margaritas. You will never worry about a crowded beach. You will swim in the crystal blue water or stay on top with our kayaks and paddleboards for exercise. Consisting of 2 homes, the main home is 1 bedroom and 1.5 baths while the other home is 2 bedrooms and 1 bath, each with a fully stocked kitchen with all new stainless steel appliances and a living room with amazing ocean views for you to enjoy. Amenities include your private heated (or cooled) salt-water pool, 4 kayaks, and 2 paddleboards, among other items. Dog friendly and in the HEART of Islamorada on Upper Matecumbe, you will be less than a mile from Publix. And, of course, the homes are 100% smoke-free. ♛ Main House (2nd Floor): King-Size Tempurpedic adjustable bed ♛ Guest House (1st Floor): Queen-Size bed ♛ Guest House (1st Floor): Queen-Size and Full-Size bed ✔ Pillows, Linens, and Sheets ✔ 50" Smart TVs with Basic Cable ✔ Closets with Hangers and Shelves ✔ Dressers with Spacious Drawers ✔ Night Stands with Alarm Clock, Wireless Charger, and Reading Lamps ✔ Luggage Racks Since there are some great restaurants and bars very close for you to enjoy, you can simply bike to them if you don't want to drive and worry about parking. Proximity is key as you are in the heart of Islamorada and very close to everything you need. You have plenty of opportunities for adventure. We supply 6 high-end 5-speed beach bikes with large tires for handling patches of sand. Islamorada Brewery is .25 miles away, and Chef Michaels is less than a mile. Brizo faucets adorn all of your sinks, and hand-painted custom art adorns the walls. There are 5 50" Smart TVs with 150 channels of programming in addition to Netflix and Prime apps. Ubiquiti Enterprise-grade WiFi covers every inch of the property for flawless high-speed internet. Our professional mosquito control system has spray heads throughout the property and keeps mosquitos at bay as they spray throughout the day. ✔ Tub Shower ✔ Towels ✔ Hair Dryer While drinking coffee in your outdoor living room, focus on the water, as there is a short window when dolphins feed on baitfish and come as close as 25' to our beach! This is the best way to start the day as you watch the sunrise. Enjoying a glass of wine out here at the end of the day brings you right back to where you started. Be sure to repeat daily. ✔ Microwave ✔ Stove ✔ Oven ✔ Toaster ✔ Blender ✔ Hot Water Kettle ✔ Coffee Makers (Keurig Machine + Drip Coffee) ✔ Refrigerator/Freezer ✔ Dishwasher ✔ Glasses ✔ Silverware ✔ Pots & Pans The rare, plush green grass is a pleasure to walk on to and from the pool....a rarity in the keys. Our gated entrance keeps your stay private and secure. Did you drive your Tesla here? GREAT! We have an onsite charger for you as well. Stay here, and you will see why we boast the best views and stay around! * We supply all linens, including beach towels * 6 high-end bikes for getting around Upper Mat * 2 Paddleboards * 2 single-person kayaks * Life vests for 6 people * 2 dual-person kayaks * Bocce Ball * Cornhole * Enterprise-grade Wifi that covers the entire estate * Tesla and NEMA 50-14 EV charger * JBL portable speaker for pool tunes * Outdoor seating, chaise lounges, and rocking chairs * Fully stocked kitchen and all proper stemware for drinks * Tempurpedic Adjustable bed in the main house * A Printer/Scanner/Copier For Use * Gated for privacy and security This is a non-smoking property. There are no fences around the pool or ocean, so it is not advised for young children. Other than the already mentioned amenities, our home also comes with the following: ✔ High-Speed Wi-Fi ✔ Self Check-In (Smart Lock) ✔ Air Conditioning ✔ Heating ✔ Laundry Room (Washer/Dryer, Iron/Board, Utility Sink) June through November is hurricane season in Florida, and travel insurance is suggested during this time frame. May through September, sargassum can be plentiful on the beach, but it is a necessary part of the fishing in the Keys. Islamorada license # VR-235 ★ COVID-19 SANITIZATION ★ The Health, safety, and well-being of our guests are of the utmost importance. For this reason, we conduct a thorough cleaning process after each check-out. ★ DOG-FRIENDLY HOME ★ Bring your furry friends along for an exciting vacation. They'll enjoy and run around the patio outdoors while you relax in the pool. A $350 dog fee applies. ★ NO SMOKING ★ Please refrain from smoking inside the home or community! Any smoking evidence will result in odor removal and furniture cleaning fees. ★ NO PARTIES/EVENTS ★ ★ BOOKING ★ A signed rental agreement and a security deposit are required for booking and following Airbnb and VRBO policies. ★ OUTDOOR CAMERAS ★ Outdoor (only) security cameras are placed in the following locations: 2 Ring and 1 camera outside of the front gate entrance, 2 at the garage facing south at the driveway and east of the garage, 1 at the main house at kayaks, and 6 at the guest house facing 1 at Tesla charger, 1 at the pool, 1 at the beach, 1 at the driveway, 1 at guesthouse door, and 1 toward main house stairs. All are to mitigate trespassers when the home is empty, and they are not monitored for theft. Weddings, parties, or any such event is not permissible on the property. Guest access By code Other things to note * Private Pool * EV Charger * 200' property line, half is a sandy beach * Beach towels provided * 4 kayaks and 2 paddleboards * 6 bikes * AMAZING views from the entire property * Gated and fenced for privacy 2 homes with their own kitchens and living rooms, the main home has 1 bedroom and 1.5 bathrooms while the guest house has 2 bedrooms with 1 bathroom.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Apr 4, 2026$1,962.45Not Available7
Apr 5, 2026$1,962.45Not Available7
Apr 6, 2026$1,311.45Not Available7
Apr 7, 2026$1,311.45Not Available7
Apr 8, 2026$1,311.45Not Available7
Apr 9, 2026$1,311.45Not Available7
Apr 10, 2026$1,311.45Not Available7
Apr 11, 2026$1,311.45Not Available7
Apr 12, 2026$1,311.45Not Available7
Apr 13, 2026$1,311.45Not Available7
Apr 14, 2026$1,311.45Not Available7
Apr 15, 2026$1,311.45Not Available7
Apr 16, 2026$1,311.45Not Available7
Apr 17, 2026$1,311.45Not Available7
Apr 18, 2026$1,311.45Available7
Apr 19, 2026$1,048.95Available7
Apr 20, 2026$1,311.45Available7
Apr 21, 2026$1,311.45Available7
Apr 22, 2026$1,311.45Available7
Apr 23, 2026$1,569.75Available7
Apr 24, 2026$1,311.45Available7
Apr 25, 2026$1,311.45Not Available7
Apr 26, 2026$1,048.95Not Available7
Apr 27, 2026$1,311.45Not Available7
Apr 28, 2026$1,311.45Not Available7
Apr 29, 2026$1,311.45Not Available7
Apr 30, 2026$1,569.75Not Available7
May 1, 2026$1,311.45Not Available7
May 2, 2026$1,311.45Available7
May 3, 2026$1,048.95Available7
May 4, 2026$1,416.45Available7
May 5, 2026$1,416.45Available7
May 6, 2026$1,416.45Available7
May 7, 2026$1,569.75Available7
May 8, 2026$1,416.45Available7
May 9, 2026$1,416.45Available7
May 10, 2026$1,048.95Available7
May 11, 2026$1,416.45Available7
May 12, 2026$1,416.45Available7
May 13, 2026$1,416.45Available7
May 14, 2026$1,569.75Available7
May 15, 2026$1,416.45Available7
May 16, 2026$1,416.45Available7
May 17, 2026$1,048.95Available7
May 18, 2026$1,416.45Available7
May 19, 2026$1,416.45Available7
May 20, 2026$1,416.45Available7
May 21, 2026$1,569.75Available7
May 22, 2026$1,416.45Available7
May 23, 2026$1,416.45Available7
May 24, 2026$1,048.95Available7
May 25, 2026$1,416.45Available7
May 26, 2026$1,416.45Available7
May 27, 2026$1,416.45Available7
May 28, 2026$1,569.75Available7
May 29, 2026$1,416.45Available7
May 30, 2026$1,416.45Available7
May 31, 2026$1,416.45Available7
Jun 1, 2026$1,416.45Available7
Jun 2, 2026$1,416.45Available7
Jun 3, 2026$1,416.45Available7
Jun 4, 2026$1,416.45Available7
Jun 5, 2026$1,416.45Available7
Jun 6, 2026$1,416.45Available7
Jun 7, 2026$1,416.45Available7
Jun 8, 2026$1,416.45Available7
Jun 9, 2026$1,416.45Available7
Jun 10, 2026$1,416.45Available7
Jun 11, 2026$1,416.45Available7
Jun 12, 2026$1,416.45Available7
Jun 13, 2026$1,416.45Available7
Jun 14, 2026$1,416.45Available7
Jun 15, 2026$1,416.45Available7
Jun 16, 2026$1,416.45Available7
Jun 17, 2026$1,416.45Available7
Jun 18, 2026$1,416.45Available7
Jun 19, 2026$1,416.45Available7
Jun 20, 2026$1,416.45Available7
Jun 21, 2026$1,416.45Available7
Jun 22, 2026$1,416.45Available7
Jun 23, 2026$1,416.45Available7
Jun 24, 2026$1,416.45Available7
Jun 25, 2026$1,416.45Available7
Jun 26, 2026$1,416.45Available7
Jun 27, 2026$1,416.45Available7
Jun 28, 2026$1,416.45Available7
Jun 29, 2026$1,416.45Available7
Jun 30, 2026$1,416.45Available7
Jul 1, 2026$1,416.45Available7
Jul 2, 2026$1,416.45Available7
Jul 3, 2026$1,416.45Available7

Where you'll sleep

Amenities

Free parking
Garden
Crib
Bathtub
Toilet
Bathtub
Shower
Bathtub

Guests love this place

5.0

based on 3 reviews

Overall rating

5
4
3
2
1
Deborah
Deborah
16 days ago

The property and location are stellar- the views of the ocean, the private beach and pool- the photographs accurately capture the privacy and beauty of the property. The large home and smaller home are both well kept up - good beds, good showers. The few issues that needed maintenance along the way were promptly addressed by Mark who was very responsive. For checkin, I would have preferred all checkin information to be within the Airbnb app 24h prior to arrival and not sent to my personal email-- instructions for two different key codes didn't arrive in my personal email until after our arrival and made for a frustrating checkin process. Would definitely stay again.

Cassandra
Cassandra
16 days ago

Beautiful home, location, and absolutely breathtaking views. Spent lots of time in the pool by the water. Mark is very responsive as well. Highly recommend to anyone who wants to spend some time in paradise! Would definitely go back.

Georgios
Georgios
16 days ago

stunningly beautiful, amazing are are just words to describe this property. you need to actually experience it to feel the beauty and calm that comes with. bicycles canoes snorkeling equipment everything you need to have the ultimate vacation. will definitely be coming back.

Where you'll be

Islamorada, Florida, 33036, United States

Immerse yourself in the effortless coastal elegance of Islamorada, where turquoise waters and maritime heritage converge. Steps away from the Hadley Resort + Marina, you can easily access world-class boating or explore the intriguing exhibits at the History of Diving Museum, situated adjacent to the property. Discover local marine life at Theater of the Sea or enjoy upscale amenities at Cheeca Lodge & Spa and Postcard Inn

Things to know

Cancellation policy

Cancel within 24 hours for a full refund.
Fair-Refund policy applies after the cancellation deadline.

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
Pets allowed.
No parties or events.

Safety & security

Check-in after 3:00 PM.
Check-out before 10:00 AM.
Maximum 8 guests.