Chesapeake Beach Resort is located in Islamorada, Florida, just two miles from Windley Key Fossil Reef Geological State Park and directly on the oceanfront, offering stunning ocean views and easy access to the beach. The resort has received very good ratings for location, cleanliness, and overall user experience. The resort offers a range of rooms and suites, all featuring a 37-inch flat-screen cable TV and a small refrigerator. Guests can enjoy an outdoor pool with ocean views, a Jacuzzi, a terrace or balcony, a garden, and a restaurant and bar on-site.
8.3 758 reviews
Islamorada, FL
09/10 – 12/10
A$506/nighttotal: A$1518 (3 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
1 2
resort , Islamorada, Village of Islands
The Postcard Inn Beach Resort & Marina is located on an island in the Florida Keys, just 3 km from Windley Key Fossil Reef Geological Park and 34 km from Key Largo. The resort has received very good ratings for user experience, location, and cleanliness. The resort offers a range of amenities and activities, including a swimming pool, a terrace, a garden, a restaurant, a bar, and a marina. Guests can enjoy fresh seafood at the Raw Bar, charter fishing trips, or explore the surrounding area by jet ski.
9.1 3678 reviews
Islamorada, FL
01/07 – 05/07
A$3229/nighttotal: A$12916 (4 )
Cheeca Lodge & Spa
2 7
resort , Islamorada, Village of Islands
Cheeca Lodge & Spa is situated on a 27-acre stretch of waterfront in Islamorada, just a 20-minute drive from downtown Key Largo and 13.7 miles from Long Key State Park. The resort has received very good user ratings, with excellent scores for location and cleanliness. The property features spacious rooms with balconies and resort views. Guests can enjoy a range of amenities, including a 9-hole golf course, spa, fishing pier, swimming pools, fitness centre, tennis courts, and watersports facilities.
This Islamorada apartment, situated on a private beach within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks, offers convenient access to local attractions. This one-bedroom, one-bathroom flat sleeps four guests comfortably, boasting two queen-size beds, a private beach, on-site amenities including a heated pool, kayaks, paddleboards, bicycles, daily continental breakfast, daily housekeeping, and free parking.
8.0 1 review
Islamorada, FL
07/08 – 23/08
A$871/nighttotal: A$13936 (16 )
1 Bedroom Suite W/kitchenette, Pool View, Free Parking & Pet Friendly
1 4
resort , Islamorada, Village of Islands
This beachfront suite, ‘Beachside Retreat In Islamorada - Suite W/ Pool View Queen | Family Ready’, is situated in Matecumbe, Islamorada, within a 2.4km walk of Indian Key Historic State Park and Bud n' Mary's Dive Centre, and under 1.6km from the Hurricane Monument and Florida Keys Brewing Co. The 42 square metre self-catering apartment offers a queen-size bed, one bathroom, sleeps six, and includes a pool, terrace, and concierge service, providing easy access to Islamorada's attractions.
Islamorada, FL
28/06 – 01/07
A$1283/nighttotal: A$3849 (3 )
4 Spacious Units! Free Parking, Pets Allowed
4 5
resort , Islamorada, Village of Islands
This Islamorada resort, offering a four-bedroom apartment, boasts private beach access and is within walking distance of the Theatre of the Sea, and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. The 1160 sq ft property sleeps up to 16 guests, features four bathrooms, a private boat ramp (fee applies), daily housekeeping, a complimentary continental breakfast, and access to an on-site heated pool, kayaks, paddleboards, and bike rentals.
10 4 reviews
Islamorada, FL
30/07 – 06/08
A$417/nighttotal: A$2919 (7 )
Perfect For Family Beach Vacation! Free Breakfast
1 2
resort , Islamorada, Village of Islands
This Islamorada apartment, situated on a private beach within a pet-friendly resort, is a short walk (less than 1km) from the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. The self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a balcony, a swimming pool, fitness centre, free parking, and daily continental breakfast and housekeeping, plus access to kayaks, paddleboards and bikes.
Islamorada, FL
28/06 – 01/07
A$1764/nighttotal: A$5292 (3 )
2 Spacious Garden Suite W/ Kitchenette | Outdoor Pool + Beach Access
2 5
resort , Islamorada, Village of Islands
This beachfront property in Matecumbe, Islamorada, offers the '2 Spacious Garden Suites W/ Kitchenette | Outdoor Pool + Beach Access' option, situated within a 2.4km walk of Indian Key Historic State Park and Bud n' Mary's Dive Centre, and under 1.6km from the Hurricane Monument and Florida Keys Brewing Co. The 57 square metre suites, each sleeping up to 12 guests, feature two bedrooms, two bathrooms, a kitchenette, a terrace/balcony, and access to an outdoor pool, plus concierge services and on-site parking.
Islamorada, FL
28/06 – 01/07
A$1765/nighttotal: A$5295 (3 )
2 Suites W/queen Beds, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly
2 5
resort , Islamorada, Village of Islands
This pet-friendly resort, offering '2 Suites W/queen Beds, Kitchenette, Outdoor Pool, Free Parking & Pet Friendly', is located in Islamorada's Matecumbe district, close to recreational parks and beaches, with convenient access to Indian Key Historic State Park and the Hurricane Monument, though precise distances aren't specified. The two-suite property sleeps up to 12 guests, each suite featuring queen-size beds, a kitchenette, and a balcony; on-site or nearby activities include watersports such as jet skiing, kayaking, and scuba diving, plus cycling.
9.2 2444 reviews
Islamorada, FL
18/07 – 22/07
A$1073/nighttotal: A$4292 (4 )
Pines & Palms Resort
2 4
resort , Islamorada, Village of Islands
Pines & Palms Resort is located in Islamorada, close to Alligator Reef and less than a mile from Miss Islamorada Fishing Charters, with John Pennekamp Coral Reef State Park a short 30-minute drive away. This resort has very good user ratings, an excellent location rating and a very good cleanliness rating. The resort offers a range of apartments with full kitchens and ocean views. Guests can enjoy a private beach, an oceanfront pool, a Tiki Bar, kayak and bike rentals, private boat docks, a covered cabana with a barbecue grill, and premium sport fishing areas.
Islamorada, FL
18/07 – 22/07
A$580/nighttotal: A$2320 (4 )
Islamorada Stay! Free Breakfast | Pool & Parking!
2 4
resort , Islamorada, Village of Islands
This Islamorada resort offers a prime location in the Village of Islands, approximately 160 kilometres south of Miami, known for its upscale, small-town atmosphere and natural beauty. The accommodation provides a 2-bedroom, 1-bathroom unit for up to 4 guests, featuring air conditioning, free Wi-Fi, a swimming pool, complimentary breakfast and parking, and welcomes pets for an additional nightly charge under the "Islamorada Stay! Free Breakfast | Pool & Parking!" offer.
10 1 review
Islamorada, FL
28/06 – 01/07
A$2175/nighttotal: A$6525 (3 )
2 Bedroom Suite In Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
2 5
resort , Islamorada, Village of Islands
This beachfront villa in Matecumbe, Islamorada, is situated a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Centre, and under 2 km from the Hurricane Monument and Florida Keys Brewing Co. The 99 square metre property boasts two bedrooms, two bathrooms, sleeps eight guests, and includes a swimming pool, terrace, and fully equipped kitchen; concierge services are also available.
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
01/07 – 05/07
A$1885/nighttotal: A$7540 (4 )
Chesapeake Beach Resort
2 7
resort , Islamorada, Village of Islands
Chesapeake Beach Resort is located in Islamorada, Florida, just two miles from Windley Key Fossil Reef Geological State Park and directly on the oceanfront, offering stunning ocean views and easy access to the beach. The resort has received very good ratings for location, cleanliness, and overall user experience. The resort offers a range of rooms and suites, all featuring a 37-inch flat-screen cable TV and a small refrigerator. Guests can enjoy an outdoor pool with ocean views, a Jacuzzi, a terrace or balcony, a garden, and a restaurant and bar on-site.
9.1 3678 reviews
Islamorada, FL
01/07 – 05/07
A$3229/nighttotal: A$12916 (4 )
Cheeca Lodge & Spa
2 7
resort , Islamorada, Village of Islands
Cheeca Lodge & Spa is situated on a 27-acre stretch of waterfront in Islamorada, just a 20-minute drive from downtown Key Largo and 13.7 miles from Long Key State Park. The resort has received very good user ratings, with excellent scores for location and cleanliness. The property features spacious rooms with balconies and resort views. Guests can enjoy a range of amenities, including a 9-hole golf course, spa, fishing pier, swimming pools, fitness centre, tennis courts, and watersports facilities.
Best Islamorada, FL resorts with a pool
Among the 69 accommodations in Islamorada, FL, here are the 4 best resorts with a pool
9.0 4004 reviews
Islamorada, FL
28/06 – 01/07
A$1472/nighttotal: A$4416 (3 )
Islander Resort
2 5
resort , Islamorada, Village of Islands
Islander Resort is situated directly on the beach in Islamorada, offering easy access to the beautiful waters of the Florida Keys and the area's attractions. The resort has received very good ratings for its overall experience, with excellent marks for its location and cleanliness. The resort provides spacious rooms with private porches or lanais, perfect for enjoying the tropical ambiance. Guests can enjoy a range of amenities including swimming pools, a bar and restaurant, a spa, a fitness centre, and a concierge service.
10 2 reviews
Islamorada, FL
28/06 – 01/07
A$602/nighttotal: A$1806 (3 )
Proximity Ats Its Best! 2 Convenient Units, Pool
2 5
resort , Islamorada, Village of Islands
This Islamorada apartment rental is situated on a private beach, within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. The 606 sq ft property comprises two bedrooms, two bathrooms, sleeps eight guests, and offers amenities including a heated pool, kayaks, paddleboards, bicycles, and complimentary continental breakfast.
Islamorada, FL
30/07 – 06/08
A$432/nighttotal: A$3024 (7 )
Rare Gem! Free Parking, Breakfast, Onsite Pool
1 2
resort , Islamorada, Village of Islands
This Islamorada resort offers direct access to a private beach and is situated conveniently close to renowned coral reefs for snorkelling and diving, Windley Key Fossil Reef Geological State Park, Lignumvitae Key Botanical State Park, the History of Diving Museum, and the Theatre of the Sea. The "Rare Gem! Free Parking, Breakfast, Onsite Pool" offer includes accommodation for two guests with one bathroom, featuring air conditioning, internet, a pet-friendly policy with additional charges, and an on-site outdoor heated swimming pool.
Islamorada, FL
17/10 – 26/10
A$5897/nighttotal: A$53073 (9 )
Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key
6 6
resort , Islamorada, Village of Islands
This oceanfront villa in Islamorada, Florida, boasts private beach access and is located 2.1km from Sea Oats Beach, 9km from Upper Matecumbe Key, and 13km from the Theatre of the Sea. This six-bedroom, four-bathroom property offers 303 square metres of living space, sleeps 20 guests, and features a heated pool, pickleball court, and well-equipped kitchen; massage treatments are available.
Frequently asked questions about resorts in Islamorada, FL
How easy is it to get to Islamorada, FL?
Getting to Islamorada is pretty straightforward. You can fly into Key West International Airport and then drive about an hour and a half, or you can drive down from Miami, which takes about four hours. If you're driving, you'll be on the famous Overseas Highway, which is a scenic drive over bridges and through islands.
What are the best resorts with a swimming pool in Islamorada, FL?
What time of year is best to stay in a resort in Islamorada, FL?
The best time to visit Islamorada is during the shoulder seasons, from April to May or September to October. The weather is still great, but the crowds are smaller and prices are usually lower. The summer months can get hot and humid, and hurricane season runs from June to November.
What are the best resorts with jacuzzi in Islamorada, FL?
What are the most romantic activities in and around Islamorada, FL?
Islamorada is a perfect destination for a romantic getaway. You can take a sunset cruise on a sailboat, have a romantic dinner at one of the many waterfront restaurants, or spend a day exploring the Indian Key Historic State Park, which is a beautiful and secluded spot. There are also lots of opportunities for fishing, kayaking, and paddleboarding.
What are the best family friendly resorts in Islamorada, FL?
What are the nearest cities to explore when you are in Islamorada, FL?
The nearest city to Islamorada is Marathon, which is about 30 minutes away. You can also easily drive to Key West (about two hours), Miami (about four hours), and Fort Lauderdale (about four and a half hours).
What are the best pet friendly resorts in Islamorada, FL?
What are the most requested amenities in resorts in Islamorada, FL?
The most requested amenities in Islamorada resorts are private balconies or patios, swimming pools, and waterfront views. Many resorts also offer on-site restaurants, bars, and spa services.
Destinations nearby
Best Islamorada, FL resorts with air conditioning
Islamorada, FL
30/07 – 06/08
A$403/nighttotal: A$2821 (7 )
Kayak In Florida Keys! Beachside Unit! Pool!
1 2
resort , Islamorada, Village of Islands
This beachside holiday let in Islamorada, Village of Islands, offers private beach access and is situated within 2 kilometres of world-class snorkelling and scuba diving on coral reefs, as well as Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. The "Kayak In Florida Keys!" offer provides a 335 sq. ft. unit with air conditioning, internet, a swimming pool, and space for two guests, with complimentary toiletries, a television, and on-site parking, while pets are permitted for an additional nightly fee.
Islamorada, FL
30/07 – 06/08
A$490/nighttotal: A$3430 (7 )
Convenient Stay, Superb Location, Free Breakfast
1 2
resort , Islamorada, Village of Islands
This Islamorada resort offers a "Convenient Stay, Superb Location, Free Breakfast" package, situated on a private beach just 200 metres from the History of Diving Museum and within easy reach of Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This family-friendly accommodation, suitable for up to four guests, features air conditioning, Wi-Fi, an outdoor heated swimming pool, and allows pets for an additional fee, with complimentary parking available.
10 1 review
Islamorada, FL
09/10 – 12/10
A$517/nighttotal: A$1551 (3 )
Large Unit W/ Private Beach Access! Free Breakfast
1 2
resort , Islamorada, Village of Islands
This Islamorada apartment, situated on a private beach within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park, offers convenient access to local attractions. The 37 square metre self-catering flat features two queen beds and a sofa bed, sleeping up to four guests, and includes a kitchenette, daily housekeeping, complimentary continental breakfast, and access to resort amenities such as a heated pool, kayaks, paddleboards, and bicycles.
9.3 49 reviews
Islamorada, FL
30/07 – 06/08
A$383/nighttotal: A$2681 (7 )
Peaceful Island Getaway In Islamorada! Parking!
1 2
resort , Islamorada, Village of Islands
This apartment is located in Islamorada, a charming seaside village known for its stunning coral reefs, and is just a short walk from the Theater of the Sea and nearby tropical forests like Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This property has received excellent ratings for its location, cleanliness, and overall experience. The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including a private beach, a heated pool with ocean views, a private boat ramp, kayaks, stand-up paddleboards, bicycles, and a daily continental breakfast.
Best Islamorada, FL resorts with a gym
8.8 873 reviews
Islamorada, FL
30/07 – 06/08
A$996/nighttotal: A$6972 (7 )
Bayside Villas By Islander Resort
1 2
resort , Islamorada, Village of Islands
Islander Bayside Villas & Boatslips is located in Islamorada, Florida, just a short walk from the beach and a short drive from Windley Key Fossil Reef Park. The resort has received very good ratings for user experience, location, and cleanliness. The villas offer a comfortable and convenient stay with fully equipped kitchens, flat-screen TVs, free WiFi, and laundry facilities. Guests can enjoy a refreshing dip in the outdoor pool, rent bicycles, and explore the nearby water sports activities.
8.7 83 reviews
Islamorada, FL
08/09 – 06/10
A$554/nighttotal: A$15512 (28 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
1 2
resort , Islamorada, Village of Islands
Three Waters Resort And Marina, a Tribute Portfolio Resort, is located in Islamorada, Florida, offering fifteen waterfront acres with convenient access to the village's attractions and the renowned sport fishing opportunities of the area. This Islamorada resort boasts diverse lodging options, including rooms and cottages, a private beach lagoon at The Cove, nine restaurants ranging from casual to upscale dining (including the Kindler and Tiki Bar), a full-service marina, a fitness centre, and a swimming pool.