1414 Vacation rentals and Airbnb in Islamorada, FL
9.7 124 reviews
Islamorada, FL
03/08 – 05/08
₹43246/nighttotal: ₹86492 (2 )
Coastal Comfort In Ocean Pointe Suites.
2 5
apartment , Tavernier
This Tavernier apartment is situated just a short walk from the end of the pier, offering stunning views of the Atlantic Ocean and Florida Keys mangroves. It has received excellent ratings for location, cleanliness, and user experience. The two-bedroom, two-bathroom apartment spans 91 square metres and can comfortably accommodate up to six guests. Amenities include a swimming pool, jacuzzi, tennis courts, a marina, a cafe, and a beach area, providing a range of activities and features for a relaxing getaway.
9.7 26 reviews
Islamorada, FL
08/09 – 06/10
₹16831/nighttotal: ₹471268 (28 )
Islamorada Getaway Townhouse
1 2
house , Islamorada, Village of Islands
This Islamorada townhouse, situated in the Village of Islands, is centrally located, minutes (less than 1.6km) from the Islamorada sandbar and acclaimed restaurants. The three-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, private swimming pool, garden, and parking; note the spiral staircase.
10 8 reviews
Islamorada, FL
27/06 – 04/07
₹54248/nighttotal: ₹379736 (7 )
Fl Keys Ocean Front Escape
1 2
apartment , Islamorada, Village of Islands
This oceanfront apartment in Islamorada, Village of Islands, offers direct sea access and is located within 500 meters of the oceanfront beach. This two-bedroom, three-bathroom property accommodates four guests and features a private rooftop deck, a new 10-meter boat dock, a heated community pool, and on-site peacock viewing.
Islamorada, FL
08/09 – 06/10
₹22442/nighttotal: ₹628376 (28 )
Beacon Reef 406
2 2
house , Islamorada, Village of Islands
Beacon Reef 406, a beachfront property in Islamorada, Village of Islands, offers direct sea views and is a short walk (approximately 0.4km) from the History of Diving Museum, with Windley Key Fossil Reef Geological State Park a 2km drive away. This two-bedroom, two-bathroom holiday home sleeps seven, boasting a fully equipped kitchen, Jacuzzi, spa, fitness centre, and free Wi-Fi; on-site parking and a 24-hour front desk add to guest convenience.
10 8 reviews
Islamorada, FL
08/09 – 06/10
₹34136/nighttotal: ₹955808 (28 )
Oceanfront Islamorada Townhome With Pool & Dock
1 2
house , Islamorada, Village of Islands
This three-bedroom, three-bathroom house in Islamorada, Village of Islands, offers comfortable accommodation for up to eight guests and includes a swimming pool, garden, and parking. The property boasts a fully equipped kitchen, air conditioning, and internet access, providing a relaxing base for exploring the Florida Keys, although precise distances to local attractions require further clarification.
10 2 reviews
Islamorada, FL
08/09 – 06/10
₹25958/nighttotal: ₹726824 (28 )
House ∙ 2 Bedrooms ∙ 6 Guests
2 2
house , Islamorada, Village of Islands
Villa Riolo, a gated oceanside property in Islamorada, Village of Islands, enjoys a canal-side location at Mile Marker 76.5, offering easy access to the ocean and other attractions in the Florida Keys. This two-bedroom, two-bathroom house sleeps six guests and boasts a private dock (suitable for boats up to 33ft), granite countertops, a fully equipped kitchen, and a balcony with stunning views; amenities include a spa, fitness centre, and bicycles.
9.4 18 reviews
Islamorada, FL
08/09 – 06/10
₹13165/nighttotal: ₹368620 (28 )
Exec Bay W/heated Pool, Marina, Beach, Pets Ok, Tennis/pickleball
3 2
house , Islamorada, Village of Islands
This Islamorada townhouse, situated at mile marker 87 in the Executive Bay Club, offers immediate access to Founder's Park and its beach, plus proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park. The 127-square-metre (1367 sq ft) property features three bedrooms sleeping six, two bathrooms, a fully equipped kitchen, a terrace with a BBQ, high-speed Wi-Fi, and access to the Executive Bay Club's pool, tennis/pickleball courts, clubhouse, private beach area, and fishing dock.
Islamorada, FL
10/07 – 15/07
₹21383/nighttotal: ₹106915 (5 )
The Flagler, Floating Villa, 2 Bedroom, Full Bath
1 6
apartment , Islamorada, Village of Islands
This Islamorada flat offers waterfront access in the upper middle Keys, placing you near local attractions in the 'Sportfishing Capital of the World'. This two-bedroom, one-bathroom holiday let accommodates up to six guests and features a heated swimming pool, on-site BBQ, a fully stocked kitchen, and direct access to the marine environment from a patio, with a rental boat fleet available for exploring the waters.
10 123 reviews
Islamorada, FL
27/06 – 04/07
₹42256/nighttotal: ₹295792 (7 )
Serenity By The Sea!! Anglers Reef With Boat Slip Available!!
2 2
house , Islamorada, Village of Islands
This two-bedroom villa is located in the gated community of Angler's Reef in Islamorada, just a short drive from the best restaurants and attractions in the Keys. The property has received excellent user ratings, reflecting its desirable location and amenities. The villa offers 128 square metres of living space, accommodating up to six guests comfortably. Guests can enjoy a private boat slip, a heated pool, two private beaches, and a range of water activities, including kayaking, paddleboarding, fishing, and boating.
9.4 79 reviews
Islamorada, FL
07/08 – 23/08
₹40755/nighttotal: ₹652080 (16 )
Oceanfront! Oceanfront! Oceanfront!
2 4
apartment , Islamorada, Village of Islands
This apartment is situated in Islamorada, just a short distance from the Florida Keys Dive Center and Mariners Hospital, offering easy access to the area's attractions. With excellent user ratings, this property promises a comfortable and enjoyable stay. The apartment spans 111 square metres and comfortably accommodates up to four guests. Amenities include a fully equipped kitchen, a private pool, a fitness centre, and a spa, ensuring a relaxing and enjoyable stay for all.
10 5 reviews
Islamorada, FL
01/01 – 31/05
₹30263/nighttotal: ₹4539450 (150 )
Yolo - You Only Live Once
"Unless You Do It Again"
1 2
apartment , Islamorada, Village of Islands
This Islamorada holiday home, located at Mile Marker 74 on White Marlin Beach, offers easy access to both Channel 2 and Channel 5 bridges, excellent for fishing enthusiasts. The 134 sq m property boasts a spacious open-plan design, sleeping up to four guests in two bedrooms, and includes a large kitchen with an island, private dock, multiple patios, a tiki hut, and full laundry facilities.
Islamorada, FL
01/01 – 31/05
₹16538/nighttotal: ₹2480700 (150 )
1 Bedroom Unit At The Palms - Ocean, Beach & Pool!
1 2
apartment , Islamorada, Village of Islands
This updated condominium, The Palms of Islamorada, is located at Mile Marker 79.9 within an oceanfront community, offering direct Atlantic views and proximity to the Alligator Reef Lighthouse. This one-bedroom, one-and-a-half-bathroom flat accommodates two guests and features a private balcony, modern appliances, a walk-in closet, and access to a communal swimming pool.
Best family friendly Islamorada, FL vacation rentals
Among the 1414 accommodations in Islamorada, FL, here are the 4 best family friendly rentals
This Plantation Key Colony flat is conveniently located in Islamorada, less than 3.2km from the Florida Keys Dive Center, Old Road Gallery, and Mariners Hospital, and within 9.6km of Islamorada County Park and Rain Barrel Village. The one-bedroom, one-bathroom apartment sleeps four, features a full kitchen with appliances, laundry facilities, a jacuzzi, parking, and a smart TV; nearby activities include diving, exploring local art galleries, and relaxing in the hot tub.
9.9 189 reviews
Islamorada, FL
07/07 – 11/07
₹41307/nighttotal: ₹165228 (4 )
Breathtaking Ocean Views! Owners Who Care. Sangria Sunrise! 10% Off Charters!
1 4
apartment , Tavernier
This Tavernier apartment is directly on the beach, just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. The property has received excellent ratings for location, cleanliness, and overall experience. The apartment is a one-bedroom, one-bathroom property with a floor area of 56 square metres, suitable for up to four guests. Amenities include a fully equipped kitchen, a swimming pool, a jacuzzi, a terrace, a garden, and parking.
9.8 174 reviews
Islamorada, FL
27/06 – 04/07
₹56675/nighttotal: ₹396725 (7 )
Oceanside Getaway: Beautiful Home With Boat Slip, Pool & Beach - Gated Community
2 2
apartment , Islamorada, Village of Islands
This waterfront property is located just two miles from Windley Key Fossil Reef Geological State Park, Rain Barrel Village, and Founders Park, offering easy access to the area's top attractions. With a user rating of 'excellent', this house is a great choice for travellers seeking a comfortable and convenient stay. This two-bedroom house can accommodate up to six guests, offering a comfortable and spacious living area. You can enjoy a private pool, garden, and a terrace, perfect for relaxing and enjoying the Florida sunshine.
10 1 review
Islamorada, FL
27/06 – 04/07
₹28160/nighttotal: ₹197120 (7 )
111 M² Condo ∙ 2 Bedrooms ∙ 4 Guests
2 2
apartment , Islamorada, Village of Islands
This Seagulls Condominiums flat in Islamorada, Village of Islands, offers direct beach access with tiki huts and grills, and is conveniently located within 1 kilometre of grocery stores, shops, restaurants, and charter services for diving and fishing. This 111 square metre, family-friendly apartment accommodates up to four guests with two bedrooms and two recently updated bathrooms, featuring air conditioning, a swimming pool, a balcony, a garden, a fitness centre, and two shaded parking spaces.
Best Islamorada, FL vacation rentals with a pool
Among the 1414 accommodations in Islamorada, FL, here are the 4 best rentals with a pool
8.4 28 reviews
Islamorada, FL
07/08 – 23/08
₹28912/nighttotal: ₹462592 (16 )
Anglers Reef Paradise
1 4
house , Islamorada, Village of Islands
Angler's Reef Resort is conveniently located in Islamorada, a short walk from Anne's Beach and within easy reach of other attractions like Upper Matecumbe Key and the Florida Keys Aquarium. This resort has excellent ratings for location, cleanliness, and overall user experience. The resort offers a range of accommodation options, including rooms with kitchens for those who prefer to self-cater. Guests can enjoy a variety of amenities, including a swimming pool, BBQ facilities, a garden, and a fitness centre.
9.8 53 reviews
Islamorada, FL
26/06 – 30/06
₹38320/nighttotal: ₹153280 (4 )
Stay & Play; Enjoy Scenic Views Ocean Pointe 5312
2 3
apartment , Tavernier
This waterfront apartment is situated in Tavernier, within easy walking distance of Baker's Cay Resort Beach and Harry Harris Park, and just a short drive from Mariners Hospital and Florida Keys Dive Center. It enjoys a peaceful location, perfect for a relaxing getaway. The apartment has received excellent guest reviews and is rated highly for its amenities and service. The apartment has two bedrooms, two bathrooms, and can comfortably accommodate up to six guests. It has a fully equipped kitchen, a terrace or balcony, a swimming pool, a spa, a tennis court, and free parking, providing everything you need for a comfortable and enjoyable stay.
10 2 reviews
Islamorada, FL
01/01 – 31/05
₹18418/nighttotal: ₹2762700 (150 )
Fishing Capital Of The World
1 2
house , Islamorada, Village of Islands
This two-bedroom townhouse is situated in a gated community of just ten homes, a short distance from Islamorada's restaurants, beaches and parks. The property boasts a private swimming pool, a boat dock, and four terraces, perfect for enjoying the Florida sunshine and stunning sunsets, and can accommodate up to six guests.
10 2 reviews
Islamorada, FL
28/06 – 01/07
₹30960/nighttotal: ₹92880 (3 )
Sunny Islamorada Den Suite | Sleeps 6
1 5
apartment , Islamorada, Village of Islands
This Islamorada resort flat offers direct access to a marina and is close to beach activities, with a laid-back coastal vibe and two private balconies providing pool and slight ocean views. Accommodating up to six guests, this apartment features a queen bed, queen sleeper sofa, and full-size sleeper sofa, with resort amenities including a heated pool, shuffleboard, pickleball, tennis, basketball, and charcoal grills, plus complimentary transport and access to Founders Park's sandy beaches and saltwater swimming area.
Frequently asked questions about holiday rentals in Islamorada, FL
What are some interesting places to visit in or near Islamorada, FL?
Islamorada is known for its beautiful beaches, so you'll want to spend some time at Anne's Beach or the Islamorada Beach Park. If you're interested in marine life, you can visit the Theater of the Sea or the Dolphin Research Center. For a bit of history, check out the History of Islamorada Museum.
What are the best Airbnb and vacation rentals in Islamorada, FL?
Which walking or cycling routes are the best in Islamorada, FL?
For a scenic walk or bike ride, try the Overseas Highway. It's a beautiful stretch of road that runs along the coast. You can also check out the Islamorada Nature Trail, which is a great option for birdwatching.
What are the most popular Airbnbs in Islamorada, FL?
What sports or outdoor activites can visitors enjoy in and around Islamorada, FL?
You can find plenty of water sports in Islamorada, like fishing, kayaking, paddleboarding, and diving. There are also opportunities for hiking, biking, and birdwatching in the area. If you're feeling adventurous, you can even try out a jet ski tour.
What are the best vacation rentals with a pool in Islamorada, FL?
What other towns or cities can be easily accessed from Islamorada, FL?
Islamorada is conveniently located near Key Largo, which is about 30 minutes away. You can also easily reach Marathon, which is about 45 minutes away. If you're looking for a bigger city, Miami is about a 2-hour drive.
What are the best rentals for families and kids in Islamorada, FL?
What amenities are commonly available in vacation rentals in Islamorada, FL?
Vacation rentals in Islamorada usually come with amenities like a private pool, hot tub, and a fully equipped kitchen. Some rentals also offer a boat dock, kayaks, and paddleboards.
What are the best rentals or Airbnbs with a jacuzzi in Islamorada, FL?
What time of year is best to rent a vacation rental Islamorada, FL?
The best time to visit Islamorada is during the winter months, from December to April, when the weather is warm and sunny. However, if you're looking for a less crowded experience, you can visit during the shoulder seasons, from April to June or September to November.
What are the local dishes in Islamorada, FL region?
Islamorada is known for its fresh seafood, so you'll want to try some of the local catches, like grouper, snapper, and mahi-mahi. You can also find delicious conch fritters, stone crab claws, and key lime pie. Don't forget to try the Florida Keys style conch chowder.
Destinations nearby
Best Islamorada, FL holiday rentals with a balcony
Islamorada, FL
09/10 – 12/10
₹39345/nighttotal: ₹118035 (3 )
Spacious Unit W/ Kitchenette & Balcony! Marina, Pets Allowed, Bike Rentals!
1 2
apartment , Islamorada, Village of Islands
This Islamorada apartment hotel boasts a central location, offering direct beach access and proximity to the History of Diving Museum and Keys History & Discovery Centre. The 37 square metre self-catering apartment sleeps four, featuring a bedroom, bathroom, fully equipped kitchenette, and a terrace with ocean views, plus access to a heated pool, kayaks, and paddleboards.
This two-bedroom apartment is situated in the Ocean Pointe Suites gated resort community in Tavernier, directly on the Atlantic Ocean, just minutes from Tavernier Creek, offering direct access to both the bay and the ocean. It has received excellent ratings for its location, cleanliness, and overall experience. The 78 square metre property comfortably accommodates up to six guests, with two bathrooms and a queen-size Murphy bed in the living room. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a terrace, a garden, parking, and internet access, as well as access to the resort's private beach, tennis courts, and waterfront café.
9.1 75 reviews
Islamorada, FL
30/07 – 06/08
₹40046/nighttotal: ₹280322 (7 )
Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar
2 2
apartment , Tavernier
This two-bedroom apartment is situated in Tavernier, just 2.4 kilometres from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful beaches of the Florida Keys. The property has received excellent ratings for location, cleanliness, and user experience. The 77 square metre apartment can comfortably accommodate up to six guests and features a well-equipped kitchen, two bathrooms, and a private pool. Guests can enjoy a range of amenities including a washing machine, air conditioning, and a garden.
9.8 288 reviews
Islamorada, FL
09/10 – 12/10
₹29244/nighttotal: ₹87732 (3 )
{Privately Owned} This 2 Bedroom Has Everything You Need.\nwith A Fantastic View.
2 2
apartment , Tavernier
This oceanfront apartment is situated in Tavernier Key, just a short distance from the charming village of Tavernier and its shops and restaurants, offering a peaceful escape in a tropical paradise setting. The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay. The apartment features two bedrooms and two bathrooms spread across 84 square metres, providing ample space for a relaxing getaway. Guests can enjoy a range of amenities including a swimming pool, Jacuzzi, terrace, garden, and parking, along with a fully equipped kitchen and access to the resort's facilities.
Best Islamorada, FL holiday rentals with parking
Islamorada, FL
01/01 – 31/05
₹9578/nighttotal: ₹1436700 (150 )
Turnkey Modern Studio In The Upper Keys Stylish, Bright & Fully Equipped!
1 2
studio , Islamorada, Village of Islands
This modern studio apartment is situated in Tavernier, within the Village of Islands, offering convenient access to Mariners Hospital and cultural attractions such as the History of Diving Museum, located just 800 meters away. This well-appointed flat accommodates two guests and features a fully equipped kitchen with a microwave, air conditioning, on-site parking, and in-unit laundry facilities, with a check-out time of 11:00 AM.
10 6 reviews
Islamorada, FL
09/10 – 12/10
₹36513/nighttotal: ₹109539 (3 )
Flip-flops & Sunshine: Islamorada Studio Escape
1 2
studio , Islamorada, Village of Islands
This Islamorada studio apartment is situated in Matecumbe, close to San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park, offering easy access to Robbie's of Islamorada and Bud n' Mary's Dive Center. The 37-square-metre (approximately 400 square feet) self-catering unit features a queen bed and twin sleeper sofa, accommodating up to three guests, and includes a kitchen with fridge, microwave, and dishwasher, a private balcony, and access to a swimming pool, parking, and free Wi-Fi.
Islamorada, FL
30/07 – 06/08
₹39836/nighttotal: ₹278852 (7 )
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking
1 2
apartment , Islamorada, Village of Islands
This beachfront resort in Islamorada's city centre is located within 2 kilometres of Windley Key Fossil Reef Geological State Park and Indian Key Historic State Park. This one-bedroom, one-bathroom apartment for two guests offers direct access to a private beach, a heated swimming pool with ocean views, complimentary continental breakfast, on-site bike and kayak rentals, outdoor BBQ facilities, lawn games, and a boat ramp, with pets allowed.
Islamorada, FL
01/01 – 31/05
₹45299/nighttotal: ₹6794850 (150 )
Waterfront Property With Beautiful Sunsets Views!
3 2
apartment , Islamorada, Village of Islands
This waterfront flat, located in the Matecumbe district of Islamorada, Village of Islands, offers views of both the Gulf and Atlantic Oceans and is within 1.2 kilometres of Indian Key Historic State Park and the Hurricane Monument. This 204 square metre apartment sleeps up to eight guests and features air conditioning, internet, a spa, parking, and direct access to water activities via an onsite boat ramp, with nearby opportunities for motor boating, sailing, fishing, and cycling.