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69 Best resorts in Islamorada, FL
8.3 758 reviews
Islamorada, FL
07/25 – 08/01
$1284/nighttotal: $8988 (7 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
2 5
resort , Islamorada, Village of Islands
The Postcard Inn Beach Resort & Marina is located on an island in the Florida Keys, just a short drive from Windley Key Fossil Reef Geological Park and Key Largo. The resort is highly rated by travelers, with excellent location, very good cleanliness, and very good overall ratings. This resort offers a unique tropical atmosphere with a marina for fishing, jet ski rentals, and water sports. Guests can enjoy the on-site Raw Bar, WiFi, parking, cable TV, private bathrooms, and safety deposit boxes in each room.
Islamorada, FL
06/28 – 07/01
$410/nighttotal: $1230 (3 )
2 Pet-friendly Units, Free Breakfast, Pool
2 5
resort , Islamorada, Village of Islands
This resort in Islamorada offers private beach access and is situated near world-class snorkeling and scuba diving on coral reefs, as well as Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This pet-friendly accommodation features 2-bedroom, 2-bathroom units, each 301 sq. ft. and accommodating up to 8 guests, with an on-site heated outdoor pool, free breakfast, and complimentary parking.
Islamorada, FL
07/18 – 07/22
$325/nighttotal: $1300 (4 )
Convenient Stay, Superb Location, Free Breakfast
1 4
resort , Islamorada, Village of Islands
This Islamorada resort offers a "Convenient Stay, Superb Location, Free Breakfast" with direct access to a private beach, proximity to renowned coral reefs for snorkeling and diving, and is within walking distance of the History of Diving Museum and Theater of the Sea, as well as close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This pet-friendly lodging accommodates up to 4 guests with 1 bathroom, features air conditioning, complimentary Wi-Fi, an outdoor heated swimming pool, and family-friendly activities, with parking available for an additional charge for pets.
This Islamorada condo is ideally located on a private beach, within walking distance of Theater of the Sea and near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks. The 290-square-foot unit features two queen beds, accommodating up to four guests, and includes amenities such as a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast, and daily housekeeping.
10 2 reviews
Islamorada, FL
10/09 – 10/12
$536/nighttotal: $1608 (3 )
Proximity Ats Its Best! 2 Convenient Units, Pool
2 2
resort , Islamorada, Village of Islands
This Islamorada, Florida vacation rental boasts two 301-square-foot bedrooms with partial ocean views, balconies, and is within walking distance of the Theater of the Sea, and near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks. The 602-square-foot apartment sleeps eight, includes two bathrooms, a private beach access, on-site amenities such as a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast, and free parking for one car.
8.0 4 reviews
Islamorada, FL
07/18 – 07/22
$408/nighttotal: $1632 (4 )
Ideal Location! Pets Allowed, Onsite Pool
2 4
resort , Islamorada, Village of Islands
This Islamorada resort, offering the "Ideal Location! Pets Allowed, Onsite Pool" package, is located approximately 60 miles south of Miami and is known for its year-round sun and proximity to world-class fishing. This two-bedroom, one-bathroom vacation rental accommodates up to four guests and features air conditioning, internet, an onsite swimming pool, and complimentary daily cleaning, with pets welcome for an additional nightly fee.
9.0 2594 reviews
Islamorada, FL
07/03 – 07/05
$865/nighttotal: $1730 (2 )
Chesapeake Beach Resort
1 5
resort , Islamorada, Village of Islands
Chesapeake Beach Resort is located in Islamorada, Florida, just two miles from Windley Key Fossil Reef Geological State Park, offering easy access to both the beach and nearby attractions. The resort consistently receives very good ratings for its location, cleanliness, and overall experience. The resort offers a variety of rooms and suites, all featuring comfortable furnishings and modern amenities. Guests can enjoy a refreshing swim in the outdoor pool, relax in the hot tub, or take advantage of the on-site restaurant, bar, and room service.
Islamorada, FL
07/09 – 07/12
$1181/nighttotal: $3543 (3 )
One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly
2 5
resort , Islamorada, Village of Islands
This pet-friendly Islamorada resort, offering the "One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly," is located in the Matecumbe district, near Indian Key Historic State Park and Hurricane Monument. The two-bedroom, two-bathroom suite sleeps up to 12 guests and features a kitchenette, balcony, free Wi-Fi, and access to on-site and nearby water sports.
10 1 review
Islamorada, FL
07/23 – 07/26
$1597/nighttotal: $4791 (3 )
3 Bedroom Suite W/kitchenette, Pool, Free Parking & Pet Friendly
3 2
resort , Islamorada, Village of Islands
This beachfront Islamorada villa in Matecumbe offers direct ocean access, a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Center, and less than 1.2 miles from the Hurricane Monument and Florida Keys Brewing Co. This 720-square-foot property boasts three bedrooms, one bathroom, sleeps eight guests, and includes a pool, terrace, concierge service, and in-villa amenities such as a refrigerator, microwave, balcony, and TV.
Islamorada, FL
07/24 – 07/26
$1224/nighttotal: $2448 (2 )
2 Spacious Garden Suite W/ Kitchenette | Outdoor Pool + Beach Access
2 2
resort , Islamorada, Village of Islands
This beachfront Islamorada vacation rental, offering the "2 Spacious Garden Suite W/ Kitchenette | Outdoor Pool + Beach Access," is centrally located in Matecumbe, a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Center, and less than a mile from the Hurricane Monument and Florida Keys Brewing Co. The 610-square-foot suite features four bedrooms, two bathrooms, sleeps twelve guests, and includes a kitchenette, private terrace, pool access, and concierge services.
9.3 3 reviews
Islamorada, FL
06/28 – 07/01
$465/nighttotal: $1395 (3 )
2 Comfortable Units, Onsite Pool, Pets Allowed
2 5
resort , Islamorada, Village of Islands
This Islamorada apartment complex is located on a private beach, just a short walk from the Theater of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. The surrounding area offers plenty of opportunities for outdoor recreation, from fishing and kayaking to exploring the unique natural beauty of the Florida Keys. This two-bedroom, two-bathroom apartment comfortably accommodates up to eight guests, making it perfect for families or groups of friends. The property offers a range of amenities, including a heated pool with ocean views, a private boat ramp, complimentary kayaks, paddleboards, and bicycles, daily housekeeping, and a continental breakfast.
Best Islamorada, FL resorts with air conditioning
8.0 1 review
Islamorada, FL
10/09 – 10/12
$1143/nighttotal: $3429 (3 )
Rare Find! 4 Pleasant Units! Free Breakfast
4 2
resort , Islamorada, Village of Islands
This Islamorada resort, offering four 290-square-foot units, boasts private beach access and is a short walk from the Theater of the Sea, near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks. Each fully furnished unit features two queen beds, accommodating up to 16 guests, with amenities including a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast, and on-site barbecue facilities.
Islamorada, FL
10/16 – 10/18
$1065/nighttotal: $2130 (2 )
4 Spacious Units! Free Parking, Pets Allowed
4 12
resort , Islamorada, Village of Islands
This Islamorada vacation rental boasts four bedrooms and four bathrooms, comfortably accommodating up to 16 guests, and is situated on a private beach, within walking distance of the Theater of the Sea and near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks. The property offers on-site amenities including a heated pool with ocean views, kayak and paddleboard rentals, bike rentals, a daily continental breakfast, and 24/7 front desk service; pet-friendly with boat ramp access (fees may apply).
Islamorada, FL
07/24 – 07/26
$377/nighttotal: $754 (2 )
Seaside Villas W/ Ocean Views & Front Porch! Pool
1 2
resort , Islamorada, Village of Islands
This resort offers the "Seaside Villas W/ Ocean Views & Front Porch!" in Islamorada, Village of Islands, featuring private beach access near coral reefs, Windley Key Fossil Reef Geological State Park, and Lignumvitae Key Botanical State Park, all within a short walk of the History of Diving Museum and Theater of the Sea. These pet-friendly accommodations provide 387 sq. ft. rooms for up to 4 guests, equipped with air conditioning, internet, and complimentary toiletries, and include access to a heated outdoor swimming pool and free parking.
Islamorada, FL
07/18 – 07/22
$497/nighttotal: $1988 (4 )
Best Place To Unwind! 2 Classy Units, Onsite Pool
2 4
resort , Islamorada, Village of Islands
This Islamorada apartment complex offers two 290-square-foot units, each with two queen beds, located on a private beach, within walking distance of Theater of the Sea and near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks. Each condo provides free parking, accommodates up to eight guests, and includes amenities such as a heated pool with ocean views, kayak and paddleboard rentals, daily continental breakfast, and daily housekeeping, plus pet-friendly access to an on-site boat ramp (fee applies).
Check Out Resorts with a Gym in Islamorada, FL
Every resort in Islamorada, FL on this list includes an on-site gym, making it easy to fit a coastal workout into your daily vacation routine.
9.0 4004 reviews
Islamorada, FL
07/03 – 07/05
$1303/nighttotal: $2606 (2 )
Islander Resort
2 5
resort , Islamorada, Village of Islands
Islander Resort is located directly on the beach in Islamorada, Village of Islands, offering easy access to the area's many attractions and activities. The resort has received excellent ratings for location, cleanliness, and overall experience. The resort offers spacious rooms with private porches and lanais, allowing guests to enjoy the beautiful views and relax in comfort. The resort features amenities such as two swimming pools, a spa, a fitness center, a restaurant, and a bar, providing plenty of opportunities for relaxation and entertainment.
9.1 3678 reviews
Islamorada, FL
07/09 – 07/12
$1245/nighttotal: $3735 (3 )
Cheeca Lodge & Spa
1 5
resort , Islamorada, Village of Islands
Cheeca Lodge & Spa is a luxurious hotel located in Islamorada, Florida, just a 20-minute drive from downtown Key Largo. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience. The hotel sits on 27 acres of lush gardens, offering a tranquil and secluded atmosphere. Guests can enjoy a variety of amenities and activities, including a 9-hole golf course, a fishing pier, swimming pools, a fitness center, tennis courts, and a full-service spa.
8.7 83 reviews
Islamorada, FL
07/25 – 08/01
$829/nighttotal: $5803 (7 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
2 5
resort , Islamorada, Village of Islands
Three Waters Resort And Marina, a Tribute Portfolio Resort, is located in Islamorada, Florida, on fifteen waterfront acres offering easy access to the village's attractions and the Sport Fishing Capital of the World. This Islamorada resort boasts various accommodations including guest rooms and cottages, plus The Cove, an adults-only area with a private beach lagoon, nine dining options ranging from casual to upscale, a full-service marina, a fitness center, and a swimming pool.
8.8 873 reviews
Islamorada, FL
07/02 – 07/05
$787/nighttotal: $2361 (3 )
Bayside Villas By Islander Resort
1 5
resort , Islamorada, Village of Islands
Islander Bayside Villas & Boatslips is located in Islamorada, just a short walk from the beach and a short drive from Windley Key Fossil Reef Park. This resort has received very good ratings for its cleanliness, location, and overall user experience. The resort offers spacious townhouses with full kitchens, perfect for families or groups. Guests can enjoy amenities such as a swimming pool, fitness center, free Wi-Fi, and laundry facilities, as well as access to water sports and bicycle rentals.
Frequently Asked Questions about resorts in Islamorada, FL
What are the top attractions in and around Islamorada, FL?
Islamorada is known for its beautiful beaches and watersports. You can't miss the Theater of the Sea, a marine park where you can see dolphins, sea lions, and other marine animals. For a taste of the local culture, visit the Islamorada History Museum. If you are looking for something more adventurous, you can go snorkeling or diving at the nearby reefs.
What are the best resorts with a swimming pool in Islamorada, FL?
Islamorada is located on the Overseas Highway, which is easily accessible by car. The drive from Miami International Airport takes about 1 hour and 45 minutes. You can also fly into Key West International Airport, which is about a 1 hour and 30 minute drive from Islamorada.
What are the best resorts with jacuzzi in Islamorada, FL?
You can easily take a day trip to Key West, which is about a 1 hour and 30 minute drive from Islamorada. You can also visit the John Pennekamp Coral Reef State Park, which is located just a short drive from Islamorada. This park offers opportunities for snorkeling, diving, and kayaking.
What are the best family friendly resorts in Islamorada, FL?
What are the most romantic activities in and around Islamorada, FL?
Islamorada is a great place for a romantic getaway. You can take a sunset cruise on the water, have dinner at a waterfront restaurant, or go for a walk on the beach. If you are looking for something more unique, you can take a private fishing charter or go on a dolphin watching tour.
What are the best pet friendly resorts in Islamorada, FL?
What are the nearest cities to explore when you are in Islamorada, FL?
The nearest major city to Islamorada is Miami, which is about a 1 hour and 45 minute drive. You can also visit Key West, which is about a 1 hour and 30 minute drive from Islamorada. Both cities offer a wide variety of attractions, restaurants, and nightlife.
What are the most requested amenities in resorts in Islamorada, FL?
Resorts in Islamorada often offer a variety of amenities, including swimming pools, private beaches, restaurants, and bars. Many resorts also offer water sports activities, such as snorkeling, diving, and kayaking. If you are looking for a more luxurious experience, you can find resorts with spa services, fitness centers, and other amenities.
Destinations nearby
Best Islamorada, FL resorts with a jacuzzi
Among the 69 accommodations in Islamorada, FL, here are the 2 best resorts with a jacuzzi
9.0 2594 reviews
Islamorada, FL
07/03 – 07/05
$865/nighttotal: $1730 (2 )
Chesapeake Beach Resort
1 5
resort , Islamorada, Village of Islands
Chesapeake Beach Resort is located in Islamorada, Florida, just two miles from Windley Key Fossil Reef Geological State Park, offering easy access to both the beach and nearby attractions. The resort consistently receives very good ratings for its location, cleanliness, and overall experience. The resort offers a variety of rooms and suites, all featuring comfortable furnishings and modern amenities. Guests can enjoy a refreshing swim in the outdoor pool, relax in the hot tub, or take advantage of the on-site restaurant, bar, and room service.
9.1 3678 reviews
Islamorada, FL
07/09 – 07/12
$1245/nighttotal: $3735 (3 )
Cheeca Lodge & Spa
1 5
resort , Islamorada, Village of Islands
Cheeca Lodge & Spa is a luxurious hotel located in Islamorada, Florida, just a 20-minute drive from downtown Key Largo. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience. The hotel sits on 27 acres of lush gardens, offering a tranquil and secluded atmosphere. Guests can enjoy a variety of amenities and activities, including a 9-hole golf course, a fishing pier, swimming pools, a fitness center, tennis courts, and a full-service spa.
Best Islamorada, FL resorts with a pool
Among the 69 accommodations in Islamorada, FL, here are the 4 best resorts with a pool
9.2 2444 reviews
Islamorada, FL
07/03 – 07/05
$1166/nighttotal: $2332 (2 )
Pines & Palms Resort
2 5
resort , Islamorada, Village of Islands
Pines & Palms Resort is located in Islamorada, Florida Keys, just a short distance from Miss Islamorada Fishing Charters and a 30-minute drive from John Pennekamp Coral Reef State Park. This resort has received very good user ratings and excellent location ratings, with guests praising its cleanliness. The resort offers a variety of accommodations, including rooms with full kitchens and private terraces. Guests can enjoy amenities like a swimming pool, Tiki Bar, and a covered cabana with a barbecue grill, as well as activities like kayaking, biking, and fishing.
Islamorada, FL
07/24 – 07/26
$377/nighttotal: $754 (2 )
Family Fun At Islamorada! Large Unit, Beach Access
1 2
resort , Islamorada, Village of Islands
The "Family Fun At Islamorada! Large Unit, Beach Access" vacation rental is situated on a private beach in Islamorada, Village of Islands, offering convenient access to coral reefs for snorkeling and scuba diving, as well as proximity to Windley Key Fossil Reef Geological State Park, Lignumvitae Key Botanical State Park, the History of Diving Museum, and Theater of the Sea. This 387 sq. ft. unit accommodates up to 4 guests and features air conditioning, internet, and an on-site heated outdoor pool, with pets welcome and free parking available.
Islamorada, FL
07/23 – 07/26
$290/nighttotal: $870 (3 )
Strong Waves At Harry Harris Beach! Marina, Pool!
1 2
resort , Islamorada, Village of Islands
The "Strong Waves At Harry Harris Beach! Marina, Pool!" offer provides direct access to a private beach in Islamorada, Village of Islands, within walking distance of the History of Diving Museum and a short distance from the Theater of the Sea and Windley Key Fossil Reef Geological State Park. This pet-friendly hotel offers 335 sq. ft. rooms with air conditioning and complimentary Wi-Fi for up to two guests, featuring a heated outdoor swimming pool, complimentary parking, and proximity to coral reefs for snorkeling and scuba diving.
Islamorada, FL
10/17 – 10/26
$4146/nighttotal: $37314 (9 )
Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key
6 6
resort , Islamorada, Village of Islands
This oceanfront Islamorada villa, near Sea Oats Beach (1.3 miles), Upper Matecumbe Key (5.6 miles), and Theater of the Sea (8.1 miles), offers private beach access and direct ocean views. This 3,260-square-foot home boasts six bedrooms, four bathrooms, sleeps twenty guests, and includes a heated pool, pickleball court, and a fully equipped kitchen.
Search Coastal Resorts near Islamorada, FL
Experience relaxing maritime vibes at seaside resorts in Islamorada, FL, positioned short distances from the local beach towns.
Islamorada, FL
07/02 – 07/05
$1706/nighttotal: $5118 (3 )
Two Bedrooms Suite W/ocean View, Pool, Free Parking & Pet Friendly
2 5
resort , Islamorada, Village of Islands
Explore 5-Star Resorts in Islamorada, FL
Experience the height of comfort in Islamorada, FL. These luxury resorts offer high-end service and a prime setting for your stay.
10 4 reviews
Islamorada, FL
07/23 – 07/26
$333/nighttotal: $999 (3 )
Perfect For Family Beach Vacation! Free Breakfast
1 2
resort , Islamorada, Village of Islands
Best Family Resorts in Islamorada, FL
Getting the resort right makes all the difference for a family trip to Islamorada, FL, with every option offering beach access and room to spread out.
9.2 2444 reviews
Islamorada, FL
07/03 – 07/05
$1166/nighttotal: $2332 (2 )
Pines & Palms Resort
2 5
resort , Islamorada, Village of Islands
9.1 3678 reviews
Islamorada, FL
07/09 – 07/12
$1245/nighttotal: $3735 (3 )
Cheeca Lodge & Spa
1 5
resort , Islamorada, Village of Islands
8.7 83 reviews
Islamorada, FL
07/25 – 08/01
$829/nighttotal: $5803 (7 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
2 5
resort , Islamorada, Village of Islands
9.0 2594 reviews
Islamorada, FL
07/03 – 07/05
$865/nighttotal: $1730 (2 )
Chesapeake Beach Resort
1 5
resort , Islamorada, Village of Islands
Search Pet-Friendly Resorts in Islamorada, FL
Your dog is just as welcome as you are; every pet-friendly waterfront resort in Islamorada, FL features dog-friendly beaches and pet washing stations.
Islamorada, FL
07/24 – 07/26
$1224/nighttotal: $2448 (2 )
2 Spacious Garden Suite W/ Kitchenette | Outdoor Pool + Beach Access
2 2
resort , Islamorada, Village of Islands
Top-Rated Resorts with Wellness in Islamorada, FL
Spa access at every resort near the water in Islamorada, FL ensures that waterside wellness is a central part of your vacation.
