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2000 sq. ft. 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.
Check-in time: 15:00
Check-out time: 10:00
Reservation Fee for credit cards (waived if paid by check): 4.00%
Registration Number: SR-235
Unique Benefits
Private beach unlike ANYWHERE in the keys, the only pool that sits ON the Atlantic ocean!
In the heart of Islamorada, walking/biking distance from anything you'd need. Upper Matecumbe hosts restaurants, Publix, the Art District, dive centers, charter fishing, boat rental, jet ski rental, museums, and much more!
Restaurants, bars, Publix, West Marine
Square Grouper, Chef Michael, Tacos Jaliscos
Living Room
Fishing Bay
Snorkeling Diving
Car Recommended
Bird Watching
Eco Tourism
Nearby Activities:
Beach
Bicycling
Boating
Deep Sea Fishing
Fishing
Jet Skiing
Kayaking
Ocean
Parasailing
Sailing
Scuba Diving
Shopping Area
Snorkeling
Surfing
Water Skiing
Zoo
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Dec 07 - Dec 12 2025 | $1,200 | 7 nights | |||
Dec 13 - Dec 19 2025 | $1,200 | 7 nights | |||
Dec 20 - Dec 21 2025 | $1,942 | 7 nights | |||
Dec 21 - Dec 22 2025 | $1,863 | 7 nights | |||
Dec 22 - Dec 23 2025 | $1,993 | 7 nights |
Fees:
Last updated on December 04, 2025
Heather R.Paradise for People & Pups
Beautiful, well-kept property in great location. Host provides all the comforts of home with a gorgeous view. We liked the mattress in the main house so much, we bought one for ourselves! Can’t wait to return.
Stayed: August 2025 Submitted: August 16, 2025
Mark P.Amazing Stay!
The property is beautiful! Best view we’ve ever had, and we’ve stayed at many resorts. The lighthouse on the horizon and if the beached shrimp boat is still out there it’s such an island vibe! The house was clean and everything was great! Will definitely recommend to our friends!
Stayed: July 2025 Submitted: August 10, 2025
Spencer & M.A Dream Wedding Venue That Felt Like Home
The Oasis in Islamorada is truly a slice of paradise. From the moment we stepped onto the property, we knew it was something special. The grounds are breathtaking—lush, peaceful, and immaculately kept. It’s the kind of place that immediately makes you feel both relaxed and enchanted, which is exactly how we felt throughout our entire wedding weekend.What truly set The Oasis apart wasn’t just the stunning backdrop—it was the warmth and care of the people behind it. The owner went above and beyond for us, helping make every detail feel personal and seamless. You can tell that he puts his heart into every couple's experience. Our families and guests couldn't stop talking about how magical everything felt, and we couldn't agree more.Being locals, it was especially meaningful for us to celebrate such an important milestone in our own backyard, and The Oasis made it feel like we were hosting loved ones in our own home. It was the perfect place to begin our lives together, and we’re already dreaming about coming back for our one-year anniversary.If you're looking for a venue that is not only stunning but also deeply personal and filled with heart, The Oasis is it. We are forever grateful.– Melissa & Spencer
Stayed: March 2025 Submitted: April 16, 2025
Cathy and Brian B.Private, Perfect, Paradise
⭐️⭐️⭐️⭐️⭐️We had the most incredible stay at this beautiful gated property in Islamorada, Florida, where my wife and I brought our family for two weeks. This stunning Oasis features two separate houses that are well maintained, providing both space and comfort for everyone.One noted highlight was definitely the fantastic pool right on the ocean, where we spent countless hours relaxing and enjoying the breathtaking views. We were delighted by the abundant seabirds and other interesting wildlife around – it really felt like a slice of paradise. The property is so peaceful and private; it was the perfect getaway.One of the best parts, for the family experience , was being able to kayak right off our private beach, exploring the serene waters at our leisure. Watching the sunrise over the ocean each morning was truly inspiring, a magical way to start each day and to relish in the Divine of God’s creative work!Although it was a family trip, we came here to celebrate our 25th wedding anniversary on Valentine’s day and we couldn’t have chosen a better spot! Renewing our commitments under the palms of the Oasis was simply unforgettable. Everything about our stay was perfect, and we can't wait to return!Thank you Mark & Doli for an amazing experience! And thank you for maintaining this property at such a high standard!---
Stayed: February 2025 Submitted: February 22, 2025
Dorothy H.Spectacular
Property is immaculate. Spectacular views. Pool is my favorite . Very private and serene. Owner is extremely accommodating and answers emails and texts almost immediately. I would highly recommend to friends and family.
Stayed: February 2025 Submitted: February 09, 2025
Stephanie B.Heaven
We stayed at the Oasis for 1 week and were fortunate enough to host our wedding on their beautiful property. Mark and Doli have an absolute dream of a property. Mark was very helpful in the process and with working with our planner. The pool, the tiki, kayaks, everything was amazing. We hope to be able to stay again in the future as we had the most relaxing and wonderful time. Thank you so much!!!
Stayed: January 2025 Submitted: January 31, 2025
Niki H.Beautiful view
We had a fantastic stay at Oasis! The view couldn’t get any better. We couldn’t have asked for a better pool situation. The home had everything we needed, and the privacy was fabulous. We will definitely return! Thank you!
Stayed: December 2024 Submitted: January 06, 2025
Stephanie B.Amazing Week in Paradise
This house could not have been more perfect! I have stayed in just about every area of Florida and this one is hard to beat. The pool was super clean and the kids had a blast playing games in the pool when we all needed a break from the salt water. The beach was so peaceful and all of the toys (paddle boards and snorkels) were well utilized. Wifi was fast and the location was right in the heart of the little town and there were endless restaurants to choose from. I cannot forget to mention the oasis hosts were super quick to respond to questions or any little things that came up. The home is made for dog lovers and our pup thought he was in heaven I am sure. I truly felt like we had our own little beach resort for a week. I can only imagine how beautiful a wedding would be at this home. They have really outdone themselves with this one.
Stayed: August 2024 Submitted: August 12, 2024
Cristi W.Everything was perfect!
We had my daughter's wedding at The Oasis and it was absolutely perfect! The place is so beautiful and kept to perfection. Mark was so great to work with leading up to the wedding and then came the morning of the wedding to make sure the grounds were picture perfect. He stayed on site for awhile in case we needed him. Every single guest commented on how beautiful the wedding was because of the gorgeous venue. I just cannot express how much this was the perfect place for her wedding. We also stayed the whole week and absolutely loved it!
Stayed: May 2024 Submitted: June 06, 2024
Meagan N.Best wedding venue!
We recently had our wedding at the Oasis and we are BEYOND amazed at how perfect it was. The house is beautiful and the beach front views are breath taking.our guests can't stop gushing about how perfect everything was. Booking the Oasis made our wedding beyond perfect. Mark was amazing to work with throughout the process, extremely kind, responsive, and helpful!
Stayed: May 2024 Submitted: May 28, 2024
Andrew D.Absolutely incredible property!
Our family needed an escape after a difficult year. This property was absolutely everything we needed to rest and recover. The owners spared no expense in making this property the “oasis” to which its name claims its name. Not that you would need to venture from the property as it “has it all”, but wow! the location of the property is central to restaurants, entertainment, and other destinations in the Keys. Look no further, whether you’re planning an event or bringing your family for two weeks!
Stayed: May 2024 Submitted: May 16, 2024
Jill H.The Oasis = OUTSTANDING!!!
We can’t give enough stars to rate our experience with hosting our daughter’s wedding at The Oasis!! I wish we could give 500 stars!! From our initial communication for a tour until our check out everything was TOP NOTCH!! The property was beautiful, private, well appointed and nothing short of perfect! Mark’s recommendations for vendors were very helpful when planning from a distance! He made sure the beach was immaculate for the big day and took care of any needs we had all week! If you are thinking of having a wedding in Islamorada…The Oasis is the perfect canvas to design your dream wedding!!!
Stayed: April 2024 Submitted: April 17, 2024
Jill H.The Oasis = OUTSTANDING!!!
We can’t give enough stars to rate our experience with hosting our daughter’s wedding at The Oasis!! I wish we could give 500 stars!! From our initial communication for a tour until our check out everything was TOP NOTCH!! The property was beautiful, private, well appointed and nothing short of perfect! Mark’s recommendations for vendors were very helpful when planning from a distance! He made sure the beach was immaculate for the big day and took care of any needs we had all week! If you are thinking of having a wedding in Islamorada…The Oasis is the perfect canvas to design your dream wedding!!!
Stayed: April 2024 Submitted: April 17, 2024
KristinaWedding week bliss
I have been fortunate enough to grow up spending every free weekend and summer in Islamorada at my families homes and it was only fitting to have my husband and I start the next journey of our life’s here as well. I am so happy we chose this property because it really was the perfect space to make our special day come to life. The property is perfect to host weddings or any events of any size. The owner Mark was only a phone call away with any questions leading up to our big day as well as any we had while staying on the property. We will forever cherish the memories we made with friends and family here.
Stayed: April 2024 Submitted: April 10, 2024
Barbara J.Stunning
When we arrived to The Oasis I was in awe of the beauty of the property! The main house is lovely very comfortable for my husband and I and the guest house was just as lovely for family that came and stayed with us for a week. The pool was just stunning on the ocean..,it was magical. Mark was a wonderful host took care of everything , we never had an issue with anything that he didn’t take care of! Can’t wait to go back to this The Oasis it really is an oasis!
Stayed: March 2024 Submitted: March 26, 2024
The Atkinson F.A Captivating Florida Keys Wedding Venue
My family and I recently had the pleasure of hosting our daughter's, Myah's wedding at The Oasis, a stunning 3-acre private estate located at 82703 Old Hwy, Islamorada, Florida. Owned and meticulously cared for by Doli and Mark, the hosts extraordinaire, The Oasis provided an enchanting backdrop for a weekend filled with love, laughter, and lifelong memories.From the moment we stepped onto the property, it was evident that The Oasis was more than just a wedding venue; it was a carefully curated haven where dreams come true. The attention to detail exhibited by Dolli and Mark in maintaining the estate is truly commendable. The lush grounds, adorned with beautifully lit palm trees, created a magical ambiance, especially in the evening when the lights shimmered, casting a warm glow over the celebration.The highlight of our wedding weekend was the breathtaking view of the Atlantic Ocean that served as a picturesque backdrop for the ceremony. The sound of the waves, the gentle sea breeze, and the golden Florida sun all contributed to the idyllic setting that every couple dreams of for their special day. The Oasis seamlessly blends natural beauty with thoughtful landscaping, creating a one-of-a-kind experience.We opted to extend our celebration over the weekend, hosting a rehearsal dinner on Friday, February 16, the wedding on Saturday, February 17, and concluding with a delightful Sunday brunch on February 18. The flexibility and versatility of The Oasis allowed for a seamless transition between events, ensuring that each moment was as special as the last.Dolli and Mark's hospitality was exceptional. Their commitment to making our experience personal and stress-free was evident in every interaction. From coordinating logistics to accommodating special requests, they went above and beyond to ensure that our celebration was nothing short of perfection.In conclusion, The Oasis at Islamorada is not just a wedding venue; it's a destination where dreams are realized, and love is celebrated in its purest form. Our daughter's wedding was nothing short of epic, thanks to the enchanting atmosphere created by Dolli and Mark. If you are seeking a wedding venue that combines natural beauty, impeccable service, and a touch of magic, The Oasis is the perfect choice. Our heartfelt thanks to Doli and Mark for creating an unforgettable experience that will be cherished by our family for a lifetime.Sincerely, Doris and George Atkinson
Stayed: February 2024 Submitted: February 21, 2024
Quinn B.Amazing wedding!
Our daughter had a PERFECT wedding here! With 220 guests, their largest to date, everything went off flawlessly and Mark was there to ensure that. The property and views are gorgeous and would highly recommend this as a place to vacation and marry to anyone. The Oasis is truly and oasis!
Stayed: November 2023 Submitted: January 13, 2024
Daniel M.Spectacular stay!
The views are unreal! The pictures and video on the website are accurate as the home and property are well cared for and the pool was simply amazing. This is a week we will remember, not only for having our wedding here but because it simply felt like paradise! If you want privacy, this place is amazing.
Stayed: December 2023 Submitted: January 13, 2024
Patty B.Perfect Wedding
My daughter had her wedding at the Oasis and we couldn't be happier with how everything went. I have to say going into this 244 people wedding, it had us very nervous with a venue we basically never heard of. We had to bring in many different venders for this event. Mark stayed thru the end of the wedding and made sure that they all had the proper electrical setups that they needed to pull off the wedding. We understood later that this was the largest wedding they ever had on the property. The morning of the wedding Mark was out there at sunrise raking the sand and making sure everything was perfect for us. Which honestly was something he promised a year ago and I was very skeptical it would happen. But as promised he was there. The two houses on the property made everything very convenient for us. The girls had their house to get ready and my husband and I had ours. Both houses are extremely clean and have everything you possibly would need. Probably the best thing though, was having your daughter tell you the morning after that every single thing went as planned. The wedding was everything she dreamed of. All of this was possible because of the Oasis.
Stayed: November 2023 Submitted: December 14, 2023
Laura Q.A slice of PARADISE!
This property was luxury and relaxation all in one! The name speaks for itself, it is truly and Oasis. This property offers two spacious houses, a pool overlooking the ocean, direct access to the ocean for paddle boarding and kayaking, a HUGE permanent tiki hut, and so much more! Islamorada was so incredibly beautiful with so much to do and so many fantastic restaurants. We celebrated our November wedding during our week stay and it was the most incredible night! Our guests could not stop raving about how stunning the property was. Mark was extremely attentive to all details the day of the wedding, ensuring everything was set up/in working order and smoothed the sand in the ceremony and reception areas for us. There was truly nothing better than having a wedding and vacation all in one! If you are looking for a private, beachfront venue to celebrate your wedding ceremony and reception – look no further than The Oasis!!!
Stayed: November 2023 Submitted: November 26, 2023
Erin H.Best experience we could have imagined!!!
We booked this property for our wedding sight unseen and we could not have been happier! The photos do not even do it justice! The property is kept in pristine condition and the view will leave you speechless. We held our wedding ceremony with the ocean view in the background and hosted our reception under the cover of the large tiki hut that is gorgeous in person and even equipped with lighting inside. We stayed all week to celebrate with our family and friends, including our fur babies. We used the picture perfect pool every day we were there. The inside of the main and guest home were in perfect condition and very comfortable for us. And again, the views, wow! Mark and Doli helped us with vendors, moving furniture, and cleaning the beach on our wedding day so we didn’t have to worry about anything. They were very kind and responsive hosts. If you are considering this property- BOOK IT! You will not regret it.
Stayed: June 2023 Submitted: July 02, 2023
Sarah B.A m a z I n g
The Oasis is an amazing piece of heaven. If you are lucky enough to stay here, then you are indeed lucky. The property is just beautiful, the owners have thought of every detail. And if you need something else, the owners do their best to make it happen. We couldn’t have been more pleased with our week here. Highly recommend!
Stayed: March 2023 Submitted: April 08, 2023
Shawn M.The name sums up this place perfectly...it is an absolute Oasis!
The Oasis house was a dream. We had our wedding there and the pictures were like out of a magazine. Not only was it a beautiful venue for our wedding, but a perfect place to honeymoon due to the luxury and privacy of this home. Plus it was nice not having to pack up the next day and go somewhere else. Everything was absolutely beautiful. Mark and Doli, the hosts did an amazing job at making sure everything was perfect for our wedding and stay and we loved Doli's paintings, they added a chic feel to the property. They offer a lot at The Oasis, from kayaks, beach games, personal cooler, and bikes; you really get the whole package. You can tell they care for the home and your experience during your stay which is hard to find in rentals. We truly loved our stay, the property, and the customer service at The Oasis.
Stayed: March 2023 Submitted: March 15, 2023
Deanna W.This was my third trip to the Oasis and it is perfect every time.
The Oasis is a spacious ocean front property. The two houses were perfect accommodations for our group of four. We were able to relax in the heated pool or in the outdoor living room. Both overlook the Atlantic. Kayaks, paddle boards and bikes were provided. We put all to good use. I highly recommend!
Stayed: February 2023 Submitted: February 12, 2023
Erin S.Unforgettable Experience
We rented the Oasis villa for our wedding and hosted a beach day, rehearsal dinner, welcome party and our ceremony & reception all onsite. From start to finish our experience with Mark and the property was outstanding. The location of the house was perfect, the accommodations were great, and the ocean view, beach and pool were just spectacular. We had tens of guests telling us this was the best wedding that they had ever attended, largely because of this incredible venue. Mark, our host, went above and beyond to ensure every last detail was absolutely perfect. We are already brainstorming with our group of friends when we can return to the house for a reunion trip. I would recommend this stay 10 out of 10 times. Mark, thank you for everything!!!
Stayed: January 2023 Submitted: February 01, 2023
Daniel L.Wow!!! What an absolutely PERFECT Wedding Venue! Paradise from start to finish!
We cannot say enough amazing things about this venue! From the property to the homes to the views to the service from Mark and Doli. We could not have asked for a more perfect day! Blows away any resort experience. Our guests are still talking about our wedding today. You will NOT be disappointed! I promise! We can’t wait to renew our vows there one day! :)
Stayed: January 2023 Submitted: January 26, 2023
Andy V.Awesome New Years Eve!
The property was very clean and in great condition. Views are spectacular, especially from the ocean side pool. Sunrises.....WOW!!! We enjoyed the kayaking and paddle-boarding in the shallow sea-grasses, and saw sand sharks, stingrays, and various other fish. The location is very convenient to many restaurants and the new Publix's store; either a short drive or a reasonable walk away. The main house is really just a one couple building, with the second house handling two couples (although you need to share one small bathroom). Great week on the beach!
Stayed: December 2022 Submitted: January 10, 2023
Member since 2021
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