Are you yearning for a month-long adventure by the beach? Head over to Islamorada, a village that consists of six islands located south of Miami. Watersports have got to be your groove on this vacation. Popularised as the Sport-fishing Capital of the World, Islamorada boasts the world’s largest fishing fleet per square mile (11 square feet). Whether you’d like to snorkel or catch the sight of dolphins, be prepared to go wet and wild. Take your time to explore the sun, sand and sea so that you don’t miss out on any of the fun! Plan an extended stay at one of these best long-term rentals in Islamorada, Florida!
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 13, 2024.
1. Waterfront home with heated pool (from USD 689)
This spacious, 176-square-metre (1,900-square-foot) home welcomes 10 guests to explore its beauty. Natural light bathes the rooms allowing guests to enjoy a cheerful start to the day. Guests are invited to take a splash in the heated, outdoor pool or laze on the sun beds. Guests also have unrestricted use of a kayak and two cruiser-style bicycles. After a fishing expedition or a stroll along the beach, simply take an outdoor shower before entering the premises.
Offers are available for monthly stays and a cleaning fee applies.
Top guest reviews
Amenities & Room:
the beautifully renovated fully stocked kitchens on both floors came in handyboth kitchens were beautiful and stocked with everything we needed2 kitchens offer great optionsthe pool was the best entertainment for our familyCleanliness:
the home is beautiful very clean and wonderfully maintainedHost:
the owner could not be more accommodating and friendlyhighly recommend this house and the owner it's just a perfect getawayunbelievable house like new great owner very easy to work withmichael is a great host tooRead more reviewsLocation:
beautiful house great pool best locationbest location for getting to the gulf or ocean by boatthe pool was definitely and added plus and the location for canal docking are just perfectthe location is perfect with access to the ocean and the bay very quickly
2. Two-storey home with private plunge pool (from USD 864)
There’s plenty to do when you check into this property, which is situated directly on the bay in Coral Cove. The secluded house is less than 1.6 kilometres (1 mile) away from dining and retail options. To make the best use of the fully equipped kitchen, guests can grab their grub from the local grocery store, The Trading Post, which is approximately 61 metres (200 feet) away.
Guests bringing a boat will have to request a dock space in advance for a fee. The property features a private patio and a heated, plunge pool that looks over the bay. Paddleboards and beach cruisers are also provided so that guests can conveniently explore the area.
Stay for a month to enjoy discounts! Do note that a cleaning fee applies.
Top guest reviews
Amenities & Room:
the open water views from the dock and pool area are fantasticboth pools are beautifully maintained & we used them frequentlythe beds sheets pillows are high end and very comfortableCleanliness:
the property was exceptionally clean and was turn-keythe house itself was beautiful clean and well keptthe house is beautifully decorated and spotlessthey house is extremely clean and decorations are well thought outHost:
giovanna was a wonderful host thoughtful communication was helpful and she has thought of it allgiovanna was the perfect hostthe house is beautiful and giovanna is a fabulous hostwe met some of the neighbors who were very polite & friendlyour host giovanna was very accommodating and had excellent communication skillsRead more reviewsLocation:
wonderful property located in an excellent location on islamorada with several restaurants and stores within walking distancethe location is also greatwe loved the location and the settingi highly recommend this locationthe location is perfect and the house is immaculate
3. Beautiful home on a dock (from USD 568)
Fancy steering your boat to check into your vacation home? Located on an 18-metre (60-foot) deep water dock in Plantation Key, this property allows you to do just that. The property also includes a porch and a wrap-around balcony. The most alluring feature is the hot tub on the deck that overlooks the waters. Founder’s Park is just 3.4 kilometres (2.1 miles) away, where you’ll find entertainment on the beach, pool, marina and dog park.
Book a stay of at least 28 nights to enjoy a monthly discount. Do note that administrative and cleaning fees apply.
Top guest reviews
Amenities & Room:
exactly as pictured very relaxing spacious good beds good linens fully stocked kitchen great viewthe hoses fish cleaning station and ample room on the deck made every adventure smoothCleanliness:
the house was clean comfortable and well stockedHost:
the home has all the amenities and the owners were easy to reachRead more reviewsLocation:
close to great restaurants and the grocery storelots of shopping and great food close by as wellthe location by land and water were greatthis was a beautiful quiet relaxing location to come back to after a day of scuba diving
4. Cosy flat at Futura Yacht Club (from USD 215)
Located in the private community of Futura Yacht Club, this unit welcomes guests for month-long stays. The club features a heated, outdoor pool and a tennis court. Within the unit, you’ll find a balcony, from where you can look over the garden while sipping on a cuppa. A fully equipped, private kitchen is at your disposal, but you’d have to use the communal washer and dryer located on your floor.
Monthly stays are entitled to a discount and a cleaning fee applies. Make your reservations early as this rental unit is a favourite with vacationers!
Top guest reviews
Amenities & Room:
the condo was very well appointed and the bed was so comfortablethe boys enjoyed fishing off the dock every night followed by a swim in the beautiful poolthe condo was nice and cozy and maintained really wellCleanliness:
condo was very clean and comfortablethe condo was very clean and was also very well stockedthis was such a clean and well appointed place to stayproperty was quiet and cleanclean all the essentials and lovely groundsHost:
joe the owner was super accommodatinggreat communication with the property owner and the boat dockage was top notch will definitely stay againRead more reviewsLocation:
the location is perfectgreat location and quiet complexhave free access to founders park beach which was also beautifulwe were in town to visit with friends and wanted a comfortable conveniently located place to stayperfect location to explore the keys and relax
5. Boutique home with access to private beaches (from USD 400)
Checking into this property grants you exclusive access to the gated community located in Anglers Reef. With 52 villas and 30 boat slips, you’d be living in luxury amongst fellow water enthusiasts. Shared amenities include a heated swimming pool, two private beaches and landscaped gardens that look over the magnificent Atlantic Ocean. Hosts have kindly provided free wifi, beach towels, as well as booklets on dining and attractions so that you can plan your stay with ease.
There’s a monthly discount to score and a cleaning fee applies.
Top guest reviews
Amenities & Room:
all appliances worked well furniture is comfy and the beds were outstandingbeautiful condo 100 feet from the pool and beachCleanliness:
the property - the house is very well laid out and is beautifully designed and spotlessly cleanthe unit itself is very nice and cleanRead more reviewsHost:
gorgeous house and the owners were greatour initial booking contact with the owners was easy and we always received quick responsethe owners were incredibly helpful and responsive with the booking
6. Luxury villa in the heart of Florida Keys (from USD 745)
Situated in Angler’s Reef, a luxurious gated community in the centre of Florida Keys, this home welcomes up to eight guests for a restful stay. The first- and second-storey feature wrap around balconies, where guests can enjoy breathtaking sea views and the soothing ocean breeze. The kitchen is fully equipped and laundry facilities are provided. You can bring your own boat and dock it in the boat slip. Otherwise, you’ll have access to kayaks loaned by the community on a first-come-first-served basis.
Monthly discounts are available for long-term stays. A cleaning fee and property damage insurance apply.
Top guest reviews
Amenities & Room:
we love this community because of the view pool & the relaxing atmospherelovely property nice views of ocean and poolour kids enjoyed the pool and the 'old school' video game table on the main levelthe pool was well maintained and our family enjoyed the time togetherthe pool was warm & wonderful tooCleanliness:
you have a beautiful and very clean homethe house was very comfortable and cleani’m not on vacation to clean a house in better condition than when i arrivedhome had everything we needed clean and well stockedHost:
the owner was wonderful and very helpfulowner and property manage were extremely helpful and quick to respondRead more reviewsLocation:
very enjoyable location and the accommodations were perfectthe location right at the pool and marina front made it even betterthe location of anglers reef gave us great access to the ocean and bay
7. Luxury home with magnificent ocean views (from USD 1479)
Live the resort life at this property! This elegant home is great for 12 guests and features amenities to keep everyone entertained. The property comes with a heated pool, sunset deck, hot tub, fire pit and outdoor grilling area for guests to make the most of the scenic views around it. From the dock area, guests also have quick access to the ocean. Additional services such as daily housekeeping and a personal chef can be arranged for a fee.
Discounts apply for a stay of at least 28 nights. Charges apply for pool maintenance and cleaning.
Top guest reviews
Amenities & Room:
indoor kitchen has only the finest appliances and a huge island that seated all 7 of usbeds were all comfortable and pantry and cupboards were stocked with basic necessitiesRead more reviewsLocation:
the secluded waterfront location is ideal for boating and water sports and close to restaurants and shopsbeautiful modern house in a great location
8. Charming home with beach access (from USD 565)
Life on the beach can’t get more fun than this! Situated in the neighbourhood of Lower Matecumbe Key, this property offers guests full access to a private beach with canal views. The whitewashed, wood-frame house on stilts will enchant you with its elegance and simplicity. The home also features a private patio, a fire pit and a barbecue grill.
Do note that the property is not suitable for children, but feel free to bring along your furry friends for a cosy gathering. Offers for month-long stays are available, and a cleaning fee applies.
Top guest reviews
Amenities & Room:
updated cute kitchen family room w/ great dock space and hot tubexpect a clean and comfortable place to relax with all the amenities you have at your housebeds were comfortable (very soft sheets) and the bunk room was perfect for the kidsCleanliness:
kitchen has everything bathroom's are updated and cleanthe house was clean well-stocked and the kitchen/living room space was wonderful for hanging outhouse is lovely well maintained and cleanHost:
this place is fantastic hosts are awesomekate was very responsive to our questions and needskate was very responsive and answered any questions at any time of the day or nightamazing location and house kate was a great host and was very responsivekate was very responsive and helpful providing tips before i even thought i needed themRead more reviewsLocation:
great location with restaurants close by and we made memories to last a lifetimeoverall a great location and beautiful homenice location comfortable beds nice dock for fishing boatkate’s place is in a wonderful locationamazing location right on the canal and a quick 2 minute drive to their private beach
Superhost
9. Custom-built home with private beach
This custom-built home comfortably fits big groups and entertains them with plenty of amenities. The house boasts a full-size lap pool and includes access to a private beach. Beach essentials including towels and umbrellas are provided for guests’ convenience. The house also includes a patio, a garden and a barbecue grill. To create new adventures each day, guests are free to access bicycles, kayaks, paddleboards and tents.
A monthly discount is provided and a cleaning fee applies.
Islamorada, Florida, United States
50.36 km (31.3 mi) from Everglades National ParkAccommodates: 10
Top guest reviews
Amenities & Room:
they really want you to be comfortable and aware of all that the area has to offerRead more reviewsLocation:
great location and perfect for families that want to spend their time outside
10. Oceanfront villa with saltwater pool (from USD 551)
Let yourself in on the expansive views at this oceanfront villa. With access to a private beach, this property allows you to enjoy spectacular sunrises over the dunes in peace. Guests are invited for a dive in the private, saltwater pool, which can be heated on prior request. The property features a private patio, a fully fenced private back garden and an outdoor dining area with a barbecue grill.
While parties are not allowed, guests can still indulge in a laid-back, alfresco dinner. Furry friends are welcome for an additional fee. A monthly discount and cleaning fee apply.
Top guest reviews
Host:
and an excellent service and attention from the hostRead more reviewsLocation:
beautiful house in great location it has everything you needthe pool is the one perfect place to spend in the house after your time on the beach
Live the island life on Islamorada
Visiting Islamorada for a week wouldn’t be enough for you to fully explore all the islands. Why not stay for a month to witness the amazing sunrises and sunsets, dig into scrumptious food and try out a variety of water sports? Make good use of our recommended long-term rentals in Islamorada to make your break count!
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