Islamorada, Florida

Beachfront Estate w/Pool,Bikes,Kayaks,& EV charger

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8 guests
3 bedrooms
4 bathrooms
2000 sqft

Skip the resorts!

8 guests
3 bedrooms
4 bathrooms
2000 sqft

  • Flexible check-in & out

    Check-in after 3:00 PM • Check-out before 10:00 AM


About this property

Skip the resorts! 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. The ONLY pool built ON TOP of the ocean! A private 100' walk-in sandy beach, uncommon for the Keys make this property unlike any other. This private estate is 2.75 acres of landscape beauty with well over palm trees that light up at night. This 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 3 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 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. We supply 8 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 Level 2 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 with over 1gig speed ✔ Self Check-In (Smart Lock) with a new code for each guest ✔ Air Conditioning in each room ✔ 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 ★ 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 front gate entrance, 2 at the garage facing south at 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 for theft, they are not monitored.

Skip the resorts! 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. The ONLY pool built ON TOP of the ocean! A private 100' walk-in sandy beach, uncommon for the Keys make this property unlike any other. This private estate is 2.75 acres of landscape beauty with well over palm trees that light up at night. This 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 3 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 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. We supply 8 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 Level 2 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 with over 1gig speed ✔ Self Check-In (Smart Lock) with a new code for each guest ✔ Air Conditioning in each room ✔ 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 ★ 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 front gate entrance, 2 at the garage facing south at 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 for theft, they are not monitored.

Availability & Pricing

Date Price (USD, excl. fees and taxes) AvailabilityMin Stay (nights)
Mar 18, 2026$695Available3
Mar 19, 2026$695Available3
Mar 20, 2026$695Available3
Mar 21, 2026$695Available3
Mar 22, 2026$695Available3
Mar 23, 2026$695Available3
Mar 24, 2026$695Available3
Mar 25, 2026$695Available3
Mar 26, 2026$695Available3
Mar 27, 2026$695Available3
Mar 28, 2026$695Available3
Mar 29, 2026$695Available3
Mar 30, 2026$695Available3
Mar 31, 2026$695Available3
Apr 1, 2026$695Available3
Apr 2, 2026$695Available3
Apr 3, 2026$695Available3
Apr 4, 2026$695Available3
Apr 5, 2026$695Available3
Apr 6, 2026$695Available3
Apr 7, 2026$695Available3
Apr 8, 2026$695Available3
Apr 9, 2026$695Available3
Apr 10, 2026$695Available3
Apr 11, 2026$695Available3
Apr 12, 2026$695Available3
Apr 13, 2026$695Available3
Apr 14, 2026$695Available3
Apr 15, 2026$695Available3
Apr 16, 2026$695Available3
Apr 17, 2026$695Available3
Apr 18, 2026$695Available3
Apr 19, 2026$695Available3
Apr 20, 2026$695Available3
Apr 21, 2026$695Available3
Apr 22, 2026$695Available3
Apr 23, 2026$695Available3
Apr 24, 2026$695Available3
Apr 25, 2026$695Available3
Apr 26, 2026$695Available3
Apr 27, 2026$695Available3
Apr 28, 2026$695Available3
Apr 29, 2026$695Available3
Apr 30, 2026$695Available3
May 1, 2026$695Available3
May 2, 2026$695Available3
May 3, 2026$695Available3
May 4, 2026$695Available3
May 5, 2026$695Available3
May 6, 2026$695Available3
May 7, 2026$695Available3
May 8, 2026$695Available3
May 9, 2026$695Available3
May 10, 2026$695Available3
May 11, 2026$695Available3
May 12, 2026$695Available3
May 13, 2026$695Available3
May 14, 2026$695Available3
May 15, 2026$695Available3
May 16, 2026$695Available3
May 17, 2026$695Available3
May 18, 2026$695Available3
May 19, 2026$695Available3
May 20, 2026$695Available3
May 21, 2026$695Available3
May 22, 2026$695Available3
May 23, 2026$695Available3
May 24, 2026$695Available3
May 25, 2026$695Available3
May 26, 2026$695Available3
May 27, 2026$695Available3
May 28, 2026$695Available3
May 29, 2026$695Available3
May 30, 2026$695Available3
May 31, 2026$695Available3
Jun 1, 2026$695Available3
Jun 2, 2026$695Available3
Jun 3, 2026$695Available3
Jun 4, 2026$695Available3
Jun 5, 2026$695Available3
Jun 6, 2026$695Available3
Jun 7, 2026$695Available3
Jun 8, 2026$695Available3
Jun 9, 2026$695Available3
Jun 10, 2026$695Available3
Jun 11, 2026$695Available3
Jun 12, 2026$695Available3
Jun 13, 2026$695Available3
Jun 14, 2026$695Available3
Jun 15, 2026$695Available3
Jun 16, 2026$695Available3

Amenities

Free parking
Crib
Bathtub
Toilet
Bathtub
Shower
Bathtub
Shower
Toilet

Where you'll sleep



Explore Islamorada, Florida

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

Here are some things which you should know before booking Beachfront Estate w/Pool,Bikes,Kayaks,& EV charger

House rules

Check-in after 3:00 PM
Check-out before 10:00 AM
8 guests maximum
Pets allowed with fee (max 2)
No smoking - fees will apply
Events not permitted
Commercial photography requires approval