Islamorada, Florida
The Oasis
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) | Availability | Min Stay (nights) |
|---|---|---|---|
| Apr 4, 2026 | $1,962.45 | Not Available | 7 |
| Apr 5, 2026 | $1,962.45 | Not Available | 7 |
| Apr 6, 2026 | $1,311.45 | Not Available | 7 |
| Apr 7, 2026 | $1,311.45 | Not Available | 7 |
| Apr 8, 2026 | $1,311.45 | Not Available | 7 |
| Apr 9, 2026 | $1,311.45 | Not Available | 7 |
| Apr 10, 2026 | $1,311.45 | Not Available | 7 |
| Apr 11, 2026 | $1,311.45 | Not Available | 7 |
| Apr 12, 2026 | $1,311.45 | Not Available | 7 |
| Apr 13, 2026 | $1,311.45 | Not Available | 7 |
| Apr 14, 2026 | $1,311.45 | Not Available | 7 |
| Apr 15, 2026 | $1,311.45 | Not Available | 7 |
| Apr 16, 2026 | $1,311.45 | Not Available | 7 |
| Apr 17, 2026 | $1,311.45 | Not Available | 7 |
| Apr 18, 2026 | $1,311.45 | Available | 7 |
| Apr 19, 2026 | $1,048.95 | Available | 7 |
| Apr 20, 2026 | $1,311.45 | Available | 7 |
| Apr 21, 2026 | $1,311.45 | Available | 7 |
| Apr 22, 2026 | $1,311.45 | Available | 7 |
| Apr 23, 2026 | $1,569.75 | Available | 7 |
| Apr 24, 2026 | $1,311.45 | Available | 7 |
| Apr 25, 2026 | $1,311.45 | Not Available | 7 |
| Apr 26, 2026 | $1,048.95 | Not Available | 7 |
| Apr 27, 2026 | $1,311.45 | Not Available | 7 |
| Apr 28, 2026 | $1,311.45 | Not Available | 7 |
| Apr 29, 2026 | $1,311.45 | Not Available | 7 |
| Apr 30, 2026 | $1,569.75 | Not Available | 7 |
| May 1, 2026 | $1,311.45 | Not Available | 7 |
| May 2, 2026 | $1,311.45 | Available | 7 |
| May 3, 2026 | $1,048.95 | Available | 7 |
| May 4, 2026 | $1,416.45 | Available | 7 |
| May 5, 2026 | $1,416.45 | Available | 7 |
| May 6, 2026 | $1,416.45 | Available | 7 |
| May 7, 2026 | $1,569.75 | Available | 7 |
| May 8, 2026 | $1,416.45 | Available | 7 |
| May 9, 2026 | $1,416.45 | Available | 7 |
| May 10, 2026 | $1,048.95 | Available | 7 |
| May 11, 2026 | $1,416.45 | Available | 7 |
| May 12, 2026 | $1,416.45 | Available | 7 |
| May 13, 2026 | $1,416.45 | Available | 7 |
| May 14, 2026 | $1,569.75 | Available | 7 |
| May 15, 2026 | $1,416.45 | Available | 7 |
| May 16, 2026 | $1,416.45 | Available | 7 |
| May 17, 2026 | $1,048.95 | Available | 7 |
| May 18, 2026 | $1,416.45 | Available | 7 |
| May 19, 2026 | $1,416.45 | Available | 7 |
| May 20, 2026 | $1,416.45 | Available | 7 |
| May 21, 2026 | $1,569.75 | Available | 7 |
| May 22, 2026 | $1,416.45 | Available | 7 |
| May 23, 2026 | $1,416.45 | Available | 7 |
| May 24, 2026 | $1,048.95 | Available | 7 |
| May 25, 2026 | $1,416.45 | Available | 7 |
| May 26, 2026 | $1,416.45 | Available | 7 |
| May 27, 2026 | $1,416.45 | Available | 7 |
| May 28, 2026 | $1,569.75 | Available | 7 |
| May 29, 2026 | $1,416.45 | Available | 7 |
| May 30, 2026 | $1,416.45 | Available | 7 |
| May 31, 2026 | $1,416.45 | Available | 7 |
| Jun 1, 2026 | $1,416.45 | Available | 7 |
| Jun 2, 2026 | $1,416.45 | Available | 7 |
| Jun 3, 2026 | $1,416.45 | Available | 7 |
| Jun 4, 2026 | $1,416.45 | Available | 7 |
| Jun 5, 2026 | $1,416.45 | Available | 7 |
| Jun 6, 2026 | $1,416.45 | Available | 7 |
| Jun 7, 2026 | $1,416.45 | Available | 7 |
| Jun 8, 2026 | $1,416.45 | Available | 7 |
| Jun 9, 2026 | $1,416.45 | Available | 7 |
| Jun 10, 2026 | $1,416.45 | Available | 7 |
| Jun 11, 2026 | $1,416.45 | Available | 7 |
| Jun 12, 2026 | $1,416.45 | Available | 7 |
| Jun 13, 2026 | $1,416.45 | Available | 7 |
| Jun 14, 2026 | $1,416.45 | Available | 7 |
| Jun 15, 2026 | $1,416.45 | Available | 7 |
| Jun 16, 2026 | $1,416.45 | Available | 7 |
| Jun 17, 2026 | $1,416.45 | Available | 7 |
| Jun 18, 2026 | $1,416.45 | Available | 7 |
| Jun 19, 2026 | $1,416.45 | Available | 7 |
| Jun 20, 2026 | $1,416.45 | Available | 7 |
| Jun 21, 2026 | $1,416.45 | Available | 7 |
| Jun 22, 2026 | $1,416.45 | Available | 7 |
| Jun 23, 2026 | $1,416.45 | Available | 7 |
| Jun 24, 2026 | $1,416.45 | Available | 7 |
| Jun 25, 2026 | $1,416.45 | Available | 7 |
| Jun 26, 2026 | $1,416.45 | Available | 7 |
| Jun 27, 2026 | $1,416.45 | Available | 7 |
| Jun 28, 2026 | $1,416.45 | Available | 7 |
| Jun 29, 2026 | $1,416.45 | Available | 7 |
| Jun 30, 2026 | $1,416.45 | Available | 7 |
| Jul 1, 2026 | $1,416.45 | Available | 7 |
| Jul 2, 2026 | $1,416.45 | Available | 7 |
| Jul 3, 2026 | $1,416.45 | Available | 7 |
Where you'll sleep
Amenities
Guests love this place
5.0
based on 3 reviews
Overall rating
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.
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.
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.
5.0
based on 3 reviews
Overall rating
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.
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.
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
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
Refundable Bookings
Cancellation deadlines:
- For stays under 15 nights, you may cancel or reschedule up to 14 days before check-in for a full refund. For stays 15 nights or longer, the cancellation window is 60 days.
- For some homes, a 30-day deadline applies — this will be clearly shown before you book.
- Cancellations must be submitted before 4 PM EST on the deadline day to qualify.
Fair-Refund Policy
If you cancel after the deadline:
- Islamorada Home Rentalsals will relist your dates and automatically refund you for any nights that rebook.
- The refund per night will be the lower of the original price or the rebooking rate. Nights that do not rebook are non-refundable.
Half-Now, Half-Later Bookings
- The first half of your payment is non-refundable.
- The second half may be refunded according to the standard cancellation policy above.
Non-Refundable Bookings
If you selected a Non-Refundable rate at checkout, the booking cannot be changed or canceled, and no refund will be issued.
Date Changes & Rebooking
Once a stay is canceled, you can't rebook the same dates yourself. If you need help choosing new dates, our Concierge team is happy to assist.
Transfers to Another Guest
You may transfer your booking to someone else at no charge. Just contact the Concierge with the new guest's name and email. The new guest must accept the transfer for it to take effect.
Policy Match Guarantee
If a better price is available for the same property on Airbnb or the owner's site, contact the Concierge — Islamorada Home Rentalsals will match it.
By completing your booking, you acknowledge and agree to Islamorada Home Rentalsals's cancellation policy.
