This Islamorada vacation home is located within 2-3 miles of Windley Key Fossil Reef Geological State Park, Rain Barrel Village, and Founders Park, with easy access to Islamorada County Park and the History of Diving Museum. This 1630-square-foot house features two bedrooms, three bathrooms, and accommodates six guests, offering a private pool, barbecue grills, and a fully equipped kitchen including a refrigerator, microwave, dishwasher, and stovetop.
9.2 358 reviews
Islamorada, FL
06/28 – 07/01
$367/nighttotal: $1101 (3 )
Ocean View Condo With Balcony/marina View
2 5
apartment , Tavernier
This 2-bedroom apartment is located in Tavernier, a short 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys beaches and a peaceful retreat from the hustle and bustle. The apartment has excellent user, location, and cleanliness ratings. The 860-square-foot apartment can comfortably accommodate up to 6 guests. Amenities include a fully equipped kitchen, a private balcony, a swimming pool, a jacuzzi, a sauna, a tennis court, and free parking.
8.8 5 reviews
Islamorada, FL
07/03 – 07/05
$553/nighttotal: $1106 (2 )
Couples' Retreat 2br W/ Ocean Views, Pool & Beach
2 5
apartment , Tavernier
This Tavernier oceanfront condo, near Key Largo and Islamorada, offers direct beach access and proximity to John Pennekamp Coral Reef State Park and the Florida Keys Dive Center. This 850-square-foot apartment features two bedrooms, two bathrooms, sleeps six, includes a full kitchen with dishwasher, and boasts resort amenities such as a swimming pool, hot tub, and tennis courts.
Islamorada, FL
06/28 – 07/01
$448/nighttotal: $1344 (3 )
Second Floor Den Suite Sleeps 6 With Stunning Marina Views
1 5
apartment , Islamorada, Village of Islands
This Islamorada, Florida vacation rental, a one-bedroom suite in Matecumbe, offers waterfront access and is near San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park. This 800-square-foot condo features a queen bed, queen sleeper sofa, and full sleeper sofa, accommodating up to five guests and includes amenities such as a heated pool, private beach access at Caloosa Cove Resort, and free use of a transportation app.
9.8 241 reviews
Islamorada, FL
07/09 – 07/12
$529/nighttotal: $1587 (3 )
Luxurious Suite+open Ocean Views+pool & Cabana Bar
2 5
apartment , Tavernier
This Tavernier apartment is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, providing easy access to the beautiful Florida Keys beaches. The apartment has received excellent ratings for location, cleanliness, and user experience. The 2-bedroom, 2-bathroom apartment comfortably accommodates up to 6 guests in its 910 square feet of space. Enjoy the convenience of a fully equipped kitchen, in-unit laundry, a private balcony, and access to a swimming pool, spa, tennis court, and BBQ grills.
Islamorada, FL
07/24 – 07/26
$395/nighttotal: $790 (2 )
Tropical Getaway | Free Breakfast & Parking | Pool
1 2
B&B , Islamorada, Village of Islands
This Islamorada bed and breakfast offers a convenient location in the Village of Islands, approximately 60 miles south of Miami, providing picturesque bay and ocean vistas and proximity to the "Sport Fishing Capital of the World." This 559 sq. ft. pet-friendly accommodation, suitable for two guests, features air conditioning, internet access, a swimming pool, and complimentary toiletries, with one parking space per room and daily cleaning services included.
Islamorada, FL
07/03 – 07/05
$466/nighttotal: $932 (2 )
1br Condo W/ Ocean View, Near Coral Reef Park
1 5
apartment , Tavernier
This oceanfront resort condo in Tavernier is located near Key Largo and Islamorada attractions, offering easy access to John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park. This 600-square-foot apartment sleeps up to six guests, featuring two bedrooms, one bathroom, a full kitchen with a dishwasher, air conditioning, a swimming pool, and on-site parking, with the option for ocean views and a balcony.
9.7 287 reviews
Islamorada, FL
07/18 – 07/22
$382/nighttotal: $1528 (4 )
Keys Deal W/cafe & Pool Bar! Up To 20% Off Oceanfront 2/2 With Private Beach
2 4
apartment , Tavernier
This Tavernier condo is located just a short walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys coastline. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment features two bedrooms and two bathrooms, accommodating up to four guests comfortably within its 850 square feet of space. Amenities include a fully equipped kitchen, a refreshing swimming pool, a relaxing Jacuzzi, and a private terrace or balcony, allowing you to enjoy the tropical surroundings.
Islamorada, FL
06/21 – 06/26
$405/nighttotal: $2025 (5 )
Ideal Mix Of Comfort And Value! Free Parking, Pool
1 2
B&B , Islamorada, Village of Islands
This beachfront resort in Islamorada, Village of Islands, offers direct access to the coast and views of the iconic Alligator Reef Lighthouse, with Anne's Beach and the History of Diving Museum located within 2 miles. This pet-friendly inn accommodates up to 4 guests in its 1 bedroom and 1 bathroom, featuring amenities like air conditioning, Wi-Fi, a swimming pool, fitness center, on-site dining, and water sports facilities.
9.8 17 reviews
Islamorada, FL
07/09 – 07/12
$381/nighttotal: $1143 (3 )
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
2 5
apartment , Tavernier
This Tavernier waterfront rental is located 0.7 miles from Harry Harris Park and within 3 miles of Mariners Hospital and the Florida Keys Dive Center. The 900-square-foot apartment features three bedrooms, two bathrooms, sleeps six, includes a fully equipped kitchen, private balcony, swimming pool, and parking, perfect for families exploring the Florida Keys.
8.7 6 reviews
Islamorada, FL
07/03 – 07/05
$691/nighttotal: $1382 (2 )
You Found It! Free Parking, Pets Allowed
1 2
B&B , Islamorada, Village of Islands
This Islamorada bed and breakfast is located directly on the beachfront, offering stunning views of Alligator Reef Lighthouse and is just a short distance from Anne's Beach, Theater of the Sea, and the History of Diving Museum. The property is situated in a tranquil area, perfect for those seeking relaxation and easy access to the island's attractions. The charming inn features a single bedroom and bathroom, accommodating up to three guests. It offers a range of amenities, including a swimming pool, a fitness center, a bar, and a complimentary American breakfast. Guests can enjoy activities like snorkeling, diving, and fishing, or explore the island on bike tours.
9.5 183 reviews
Islamorada, FL
07/23 – 07/26
$271/nighttotal: $813 (3 )
Floating 1bd 1ba Private Cottage - Mako
1 2
apartment , Islamorada, Village of Islands
This charming cottage is located in Islamorada, close to the village center, offering easy access to restaurants, shops, and other attractions. The cottage has excellent user, location, and cleanliness ratings. This cozy rental sleeps up to three guests and features a well-equipped kitchen, air conditioning, and a private garden. Enjoy the beautiful Florida Keys weather, explore the surrounding waters on a rented boat, and take advantage of the discounted boat rental rates.
Search Family Short-Term Rentals in Islamorada, FL
Family beach days in Islamorada, FL are easier when your rental offers enough square footage for everyone to relax.
10 3 reviews
Islamorada, FL
06/20 – 06/27
$794/nighttotal: $5558 (7 )
208 M² Condo ∙ 5 Bedrooms ∙ 12 Guests
5 6
apartment , Islamorada, Village of Islands
Sandglass 4, a bayside townhouse in Islamorada's Lower Matecumbe district at mile marker 74.9, offers direct Florida Bay access with a private boat ramp and dockage for boats up to 30 feet. This 2240-square-foot Islamorada vacation rental boasts five bedrooms, three bathrooms, sleeps twelve, and includes a large kitchen, screened balcony with 180-degree ocean views, a spa, fitness center, and contactless check-in/out.
10 158 reviews
Islamorada, FL
06/20 – 06/27
$430/nighttotal: $3010 (7 )
Aquamarine Oceanview+special Rates+\ndock+pool+gym+spa+1535 Star Reviews!!!
2 2
apartment , Islamorada, Village of Islands
This waterfront apartment in Matecumbe, Islamorada, offers a unique 5-star experience with its private dock, heated pool, hot tub, and lighted tennis courts. It is highly rated by previous guests for its cleanliness, comfort, and amenities. The apartment features 2 bedrooms, 3 bathrooms, and a floor area of 1700 square feet, comfortably accommodating up to 6 guests. It boasts a fully equipped kitchen, a spacious living area, and a private terrace overlooking the water. Guests can enjoy complimentary amenities such as bikes, pool toys, and a freezer for bait/catch, as well as access to a concierge service for assistance with activities and arrangements.
9.3 124 reviews
Islamorada, FL
07/18 – 07/22
$470/nighttotal: $1880 (4 )
Oceanfront Views At Ocean Pointe + Pool + Beach & Marina Access, Updated 2br
2 4
apartment , Tavernier
This Tavernier vacation rental is conveniently located within walking distance of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to Tavernier's most popular attractions. The property has received excellent ratings for location, cleanliness, and user experience. This 2-bedroom, 2-bathroom apartment comfortably accommodates up to 6 guests in its 840 square feet of space. Guests can enjoy amenities such as a private pool, a spa tub, a fully equipped kitchen, and a balcony.
9.1 74 reviews
Islamorada, FL
07/09 – 07/12
$387/nighttotal: $1161 (3 )
Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar
2 5
apartment , Tavernier
This apartment in Tavernier is a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. It is highly rated for its location, cleanliness, and user experience. The apartment has two bedrooms, two bathrooms, a sofa bed, and a floor area of 830 square feet. It can accommodate up to six guests. Amenities include a private pool, concierge services, barbecue grills, a washing machine, and a smoke-free environment.
This oceanfront vacation home is located in the Matecumbe district of Islamorada, just a half mile from Robbie's of Islamorada and a short paddle from Alligator Reef Lighthouse. The property is rated excellent by previous guests and offers exceptional privacy and natural beauty on a private beach with a natural seawall. This 5-bedroom, 5-bathroom home comfortably accommodates up to 10 guests and offers 2,450 square feet of living space. Enjoy the private oceanfront pool, paddleboards, kayaks, fishing dock, and a well-equipped kitchen with a fridge, microwave, and dishwasher.
9.2 30 reviews
Islamorada, FL
07/25 – 08/01
$405/nighttotal: $2835 (7 )
2402 Ocean Pointe - 2 Bedroom Condo Upgraded With Clean Lines And Coastal Colors
2 5
apartment , Tavernier
This Tavernier condo, near Harry Harris Park, Mariners Hospital, and Pigeon Key, offers easy access to recreation, healthcare, and historical sites. The 850-square-foot unit features two bedrooms, two bathrooms, a sofa bed accommodating up to six guests, and amenities including a pool, jacuzzi, and free Wi-Fi.
This family-friendly condo building is located on the waterfront in Islamorada, just a mile from Sunset Drive Beach and Anne's Beach, and a short drive from San Pedro Underwater Archaeological Preserve State Park. The apartment has received excellent ratings for user experience, location, and cleanliness. This 3-bedroom, 2020 square foot apartment comfortably accommodates up to 6 guests. Enjoy amenities such as a private pool, a fenced yard, a fitness center, a spa tub, and barbecue grills, as well as a full kitchen and internet access.
Islamorada, FL
09/08 – 10/06
$200/nighttotal: $5600 (28 )
118 M² Condo ∙ 2 Bedrooms ∙ 4 Guests
2 4
apartment , Islamorada, Village of Islands
This oceanfront condo in Islamorada, the Sport Fishing Capital of the World, offers direct beach and water access. This 1270 sq ft, 2-bedroom, 2-bathroom condo accommodates up to 4 guests and features a gourmet kitchen, private dock with boat slips and tiki hut, community pool, spa, fitness center, and BBQ area.
Frequently Asked Questions about short term rentals in Islamorada, FL
What notable natural landmarks are near Islamorada, FL?
You're right in the heart of the Florida Keys, so there's no shortage of natural beauty! Head to Indian Key Historic State Park for a glimpse of the past. The Florida Keys National Marine Sanctuary is a must-see for anyone who loves to snorkel or dive. And don't forget to check out the John Pennekamp Coral Reef State Park, where you can see the Christ of the Abyss statue.
What are the best short term rentals in Islamorada, FL?
What kind of weather can travelers expect in Islamorada, FL?
Islamorada has a tropical climate, so expect warm temperatures year-round. The average high in the summer is around 88 degrees Fahrenheit, and the average low in the winter is around 65 degrees Fahrenheit. We get a lot of sunshine, but we also get some rain, especially during the summer months.
What are the best short term rentals with a pool in Islamorada, FL?
This vacation home is located in the tranquil Matecumbe district of Islamorada, Village of Islands, within walking distance of Sunset Drive Beach and San Pedro Underwater Archaeological Preserve State Park. The house has received excellent user ratings. The house has 2 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. It features a fully equipped kitchen, a private balcony, a garden, and air conditioning. Guests can enjoy activities such as swimming, sunbathing, water sports, and diving.
Islamorada, FL
07/03 – 07/05
$571/nighttotal: $1142 (2 )
Ocean View 2br Condo Pool, Beach, Near The Fun
2 5
apartment , Tavernier
This Tavernier oceanfront condo, near Key Largo and Islamorada, provides private beach access and proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park. This 850-square-foot rental boasts two bedrooms, two bathrooms, sleeps six, and includes a full kitchen, swimming pool, and parking; resort amenities such as a Jr. Olympic pool, hot tub, and tennis courts are also available.
10 121 reviews
Islamorada, FL
10/17 – 10/26
$614/nighttotal: $5526 (9 )
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip. Islamorada, Fl
4 6
apartment , Islamorada, Village of Islands
This boat is located in Angler's Reef, a gated community in Islamorada, just a short distance from the Florida Keys Brewing Co. and Florida Keys Dive Center, making it a convenient base for exploring the area. It has received excellent user ratings, so you can be sure of a comfortable stay. This spacious vacation rental offers 1980 square feet of living space and can accommodate up to 8 guests, making it ideal for families or groups of friends. The boat features a fully equipped kitchen, a private pool, a hot tub, and a spacious terrace, providing everything you need for a relaxing and enjoyable vacation.
9.8 8 reviews
Islamorada, FL
07/03 – 07/10
$2916/nighttotal: $20412 (7 )
Islamorada Beach | Beachfront, Fire Pit & Pool
1 8
apartment , Islamorada, Village of Islands
Wander Islamorada Beach, a beachfront property in Islamorada, Florida, offers direct access to a secluded cove and is conveniently located near other Village of Islands attractions. This three-story house boasts six bedrooms, five bathrooms, and three living rooms, comfortably accommodating up to twelve guests, and includes amenities such as a private pool, two outdoor terraces, two paddle boards, two kayaks, a fully equipped kitchen, and high-speed Wi-Fi.
Best Islamorada, FL lodging with laundry available
This oceanfront Tavernier condo, located 0.6 miles from Harry Harris Park and within 3 miles of Mariners Hospital and the Florida Keys Dive Center, offers stunning ocean views and easy beach access. The 830-square-foot rental boasts three bedrooms, two bathrooms, sleeps five, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and on-site barbecue grills.
10 4 reviews
Islamorada, FL
09/08 – 10/06
$256/nighttotal: $7168 (28 )
Life On A Rock Luxury Home In Downtown Islamorada
1 4
apartment , Islamorada, Village of Islands
This Islamorada condo offers immediate access to dining, entertainment, and shopping venues, with a neighborhood beach located approximately 1,320 feet away. This 2-bedroom, 2-bathroom unit accommodates up to 4 guests and features Tommy Bahama furnishings, Tempur-Pedic mattresses, air conditioning, internet, kitchen, and parking.
This beautiful vacation rental is located in Islamorada, just a short drive from the popular Islamorada Fish Company and the Theater of the Sea. The accommodation has received excellent ratings for its location, cleanliness, and overall experience. This 3-bedroom home can accommodate up to 8 guests and features a spacious 2,000 square foot layout. Guests will enjoy a private beach, an oceanfront pool, a fitness center, a spa, and a variety of other amenities.
9.7 28 reviews
Islamorada, FL
08/09 – 08/14
$360/nighttotal: $1800 (5 )
Islamorada Bungalow #5
1 2
apartment , Islamorada, Village of Islands
This Islamorada, Florida bungalow offers a convenient, centrally located base for exploring the Village of Islands, providing easy access to nearby beaches and renowned fishing spots. The 2-bedroom, 1-bathroom house sleeps 4, features a fully equipped kitchen, in-unit laundry, a private patio, community pool access, and on-site bicycles for guest use.