10 Best Long-Term Rentals In Islamorada, Florida - Updated 2024

Stacy
Stacy  
Contributing Writer
Updated
| 5 min read

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 May 31, 2024.

1. Waterfront home with heated pool (from USD 675)

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.

Stayed at this property?
Islamorada, Florida, United States
48.06 km (29.9 mi) from Everglades National Park
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
the beautifully renovated fully stocked kitchens on both floors came in handy
both kitchens were beautiful and stocked with everything we needed
2 kitchens offer great options
the pool was the best entertainment for our family
Cleanliness:
the home is beautiful very clean and wonderfully maintained
Host:
the owner could not be more accommodating and friendly
highly recommend this house and the owner it's just a perfect getaway
unbelievable house like new great owner very easy to work with
michael is a great host too
Location:
beautiful house great pool best location
best location for getting to the gulf or ocean by boat
the pool was definitely and added plus and the location for canal docking are just perfect
the location is perfect with access to the ocean and the bay very quickly
Read more reviews

2. Two-storey home with private plunge pool (from USD 721)

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.

Stayed at this property?
Islamorada, Florida, United States
48.75 km (30.3 mi) from Everglades National Park
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
the open water views from the dock and pool area are fantastic
both pools are beautifully maintained & we used them frequently
the beds sheets pillows are high end and very comfortable
Cleanliness:
the property was exceptionally clean and was turn-key
the house itself was beautiful clean and well kept
the house is beautifully decorated and spotless
they house is extremely clean and decorations are well thought out
Host:
giovanna was a wonderful host thoughtful communication was helpful and she has thought of it all
giovanna was the perfect host
the house is beautiful and giovanna is a fabulous host
we met some of the neighbors who were very polite & friendly
our host giovanna was very accommodating and had excellent communication skills
Location:
wonderful property located in an excellent location on islamorada with several restaurants and stores within walking distance
the location is also great
we loved the location and the setting
i highly recommend this location
the location is perfect and the house is immaculate
Read more reviews

3. Beautiful home on a dock (from USD 558)

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.

Stayed at this property?
Plantation Key, Florida, United States
48.37 km (30.1 mi) from Everglades National Park
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
exactly as pictured very relaxing spacious good beds good linens fully stocked kitchen great view
the hoses fish cleaning station and ample room on the deck made every adventure smooth
Cleanliness:
the house was clean comfortable and well stocked
Host:
the home has all the amenities and the owners were easy to reach
Location:
close to great restaurants and the grocery store
lots of shopping and great food close by as well
the location by land and water were great
this was a beautiful quiet relaxing location to come back to after a day of scuba diving
Read more reviews

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!

Stayed at this property?
Tavernier, Florida, United States
49.04 km (30.5 mi) from Everglades National Park
condo 6 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
the condo was very well appointed and the bed was so comfortable
the boys enjoyed fishing off the dock every night followed by a swim in the beautiful pool
the condo was nice and cozy and maintained really well
Cleanliness:
condo was very clean and comfortable
the condo was very clean and was also very well stocked
this was such a clean and well appointed place to stay
property was quiet and clean
clean all the essentials and lovely grounds
Host:
joe the owner was super accommodating
great communication with the property owner and the boat dockage was top notch will definitely stay again
Location:
the location is perfect
great location and quiet complex
have free access to founders park beach which was also beautiful
we were in town to visit with friends and wanted a comfortable conveniently located place to stay
perfect location to explore the keys and relax
Read more reviews

5. Boutique home with access to private beaches (from USD 429)

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.

Stayed at this property?
Islamorada, Florida, United States
48.44 km (30.1 mi) from Everglades National Park
PRIVATE VACATION HOME 4 Guests 2 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
all appliances worked well furniture is comfy and the beds were outstanding
beautiful condo 100 feet from the pool and beach
Cleanliness:
the property - the house is very well laid out and is beautifully designed and spotlessly clean
the unit itself is very nice and clean
Host:
gorgeous house and the owners were great
our initial booking contact with the owners was easy and we always received quick response
the owners were incredibly helpful and responsive with the booking
Read more reviews

6. Luxury villa in the heart of Florida Keys (from USD 695)

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.

Stayed at this property?
Islamorada, Florida, United States
48.47 km (30.2 mi) from Everglades National Park
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
we love this community because of the view pool & the relaxing atmosphere
lovely property nice views of ocean and pool
our kids enjoyed the pool and the 'old school' video game table on the main level
the pool was well maintained and our family enjoyed the time together
the pool was warm & wonderful too
Cleanliness:
you have a beautiful and very clean home
the house was very comfortable and clean
i’m not on vacation to clean a house in better condition than when i arrived
home had everything we needed clean and well stocked
Host:
the owner was wonderful and very helpful
owner and property manage were extremely helpful and quick to respond
Location:
very enjoyable location and the accommodations were perfect
the location right at the pool and marina front made it even better
the location of anglers reef gave us great access to the ocean and bay
Read more reviews

7. Luxury home with magnificent ocean views (from USD 1214)

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.

Stayed at this property?
Tavernier, Florida, United States
48.62 km (30.3 mi) from Everglades National Park
PRIVATE VACATION HOME 12 Guests 4 Bedrooms 6 Bathrooms

Top guest reviews
Amenities & Room:
indoor kitchen has only the finest appliances and a huge island that seated all 7 of us
beds were all comfortable and pantry and cupboards were stocked with basic necessities
Location:
the secluded waterfront location is ideal for boating and water sports and close to restaurants and shops
beautiful modern house in a great location
Read more reviews

8. Charming home with beach access (from USD 11865)

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.

Stayed at this property?
Islamorada, Florida, United States
50.48 km (31.4 mi) from Everglades National Park
30 reviews   Superhost Wifi Available
ENTIRE HOME 8 Beds 10 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
updated cute kitchen family room w/ great dock space and hot tub
expect a clean and comfortable place to relax with all the amenities you have at your house
beds were comfortable (very soft sheets) and the bunk room was perfect for the kids
Cleanliness:
kitchen has everything bathroom's are updated and clean
the house was clean well-stocked and the kitchen/living room space was wonderful for hanging out
house is lovely well maintained and clean
Host:
this place is fantastic hosts are awesome
kate was very responsive to our questions and needs
kate was very responsive and answered any questions at any time of the day or night
amazing location and house kate was a great host and was very responsive
kate was very responsive and helpful providing tips before i even thought i needed them
Location:
great location with restaurants close by and we made memories to last a lifetime
overall a great location and beautiful home
nice location comfortable beds nice dock for fishing boat
kate’s place is in a wonderful location
amazing location right on the canal and a quick 2 minute drive to their private beach
Read more reviews

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.

Stayed at this property?
Islamorada, Florida, United States
50.36 km (31.3 mi) from Everglades National Park
10 reviews   Wifi Available
ENTIRE HOME 6 Beds 10 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 10

Top guest reviews
Amenities & Room:
they really want you to be comfortable and aware of all that the area has to offer
Location:
great location and perfect for families that want to spend their time outside
Read more reviews

10. Oceanfront villa with saltwater pool (from USD 1078)

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.

Stayed at this property?
Islamorada, Florida, United States
50.55 km (31.5 mi) from Everglades National Park
45 reviews   Superhost Wifi Available
Entire villa 9 Beds 16 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Host:
and an excellent service and attention from the host
Location:
beautiful house in great location it has everything you need
the pool is the one perfect place to spend in the house after your time on the beach
Read more reviews

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!

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

History


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Stacy lives to see the world. She does minimal planning for her travels and loves walking wherever her feet takes her. Having lived in the fast-paced cities of New York, London, Shanghai and...Read more

 Want to contribute as a Local Expert?
Explore Islamorada
x
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.