Modish Unit Steps To Windley Key Fossil Reef! Pool
1 2
resort , Islamorada, Village of Islands
The Modish Unit Steps To Windley Key Fossil Reef! Pool is a holiday let situated in a private beach area of Islamorada, Village of Islands, offering direct access to coral reefs ideal for diving and snorkelling, and is a short walk to the Theater of the Sea. This pet-friendly accommodation, suitable for two guests, features a private beach, an outdoor heated swimming pool, air conditioning, complimentary toiletries, a kitchen, and on-site parking, with rooms measuring 31 square metres.
Islamorada, FL
03/07 – 05/07
NZ$773/nighttotal: NZ$1546 (2 )
Large Unit Near Secret Beach! Free Breakfast
1 2
resort , Islamorada, Village of Islands
This Islamorada resort offers the "Large Unit Near Secret Beach! Free Breakfast" deal, situated on a private beach with direct access to coral reefs, just 700 meters from the History of Diving Museum and within walking distance of the Theater of the Sea, and a short drive to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This pet-friendly accommodation, suitable for up to four guests, provides 33 square meters of living space, air conditioning, internet, a swimming pool, and complimentary parking, with cleaning services included and an additional charge for pets.
8.0 1 review
Islamorada, FL
16/10 – 18/10
NZ$1893/nighttotal: NZ$3786 (2 )
Rare Find! 4 Pleasant Units! Free Breakfast
4 12
resort , Islamorada, Village of Islands
This Islamorada apartment rental, situated in the Village of Islands, offers private beach access within a pet-friendly resort, a short walk from the Theatre of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. The 4-bedroom, 4-bathroom property boasts 290 sq ft units (approximately 27 sq m) with two queen beds each, sleeping up to 16 guests and including a heated pool, kayaks, paddleboards, bicycles, daily continental breakfast, and complimentary parking.
8.7 83 reviews
Islamorada, FL
25/07 – 01/08
NZ$1426/nighttotal: NZ$9982 (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, 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.
10 1 review
Islamorada, FL
18/07 – 22/07
NZ$978/nighttotal: NZ$3912 (4 )
Spacious 1br Suite W/kitchenette, Outdoor Pool, Free Parking & Pet Friendly
1 4
resort , Islamorada, Village of Islands
This Islamorada resort, in the Matecumbe district, offers the 'Steps Away From The Beach | Spacious 1br Suite W\/ Kitchenette' option, conveniently located near Sea Oats Beach and a short drive from the Hurricane Monument and Indian Key Historic State Park. The 57 square metre apartment features a one-bedroom suite sleeping up to six guests, boasting a kitchenette, balcony, and access to an on-site pool, restaurant, bar, boat slips, and complimentary water sports equipment; pet-friendly accommodation is also available.
Islamorada, FL
03/07 – 05/07
NZ$773/nighttotal: NZ$1546 (2 )
Villa W/ Ocean Views & Front Porch! Free Breakfast
1 2
resort , Islamorada, Village of Islands
This villa in Islamorada, Village of Islands, offers direct access to a private beach and is conveniently located within 2 kilometers of world-renowned coral reefs for snorkelling and scuba diving, Windley Key Fossil Reef Geological State Park, and Lignumvitae Key Botanical State Park. The pet-friendly accommodation, named "Villa W/ Ocean Views & Front Porch! Free Breakfast," accommodates up to four guests with one bathroom, features air conditioning and Wi-Fi, and provides a heated outdoor swimming pool and complimentary on-site parking.
9.3 49 reviews
Islamorada, FL
18/07 – 22/07
NZ$428/nighttotal: NZ$1712 (4 )
Peaceful Island Getaway In Islamorada! Parking!
1 4
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.
Islamorada, FL
28/06 – 01/07
NZ$2437/nighttotal: NZ$7311 (3 )
2 Separate Unites W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool
4 5
resort , Islamorada, Village of Islands
This four-bedroom, two-bathroom holiday property, offering '2 Separate Units W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool', is located in Islamorada's Matecumbe district, near Indian Key Historic State Park and the Hurricane Monument. The self-catering villa, sleeping up to 16 guests, boasts a pool, free Wi-Fi, and balconies with views, plus easy access to watersports such as jet skiing and kayaking in the nearby waters.
9.1 3678 reviews
Islamorada, FL
09/08 – 14/08
NZ$413/nighttotal: NZ$2065 (5 )
Cheeca Lodge & Spa
1 2
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.
8.0 1 review
Islamorada, FL
09/07 – 12/07
NZ$1207/nighttotal: NZ$3621 (3 )
1 Bedroom Suite W/kitchenette, Pool View, Free Parking & Pet Friendly
1 5
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.
10 1 review
Islamorada, FL
24/07 – 26/07
NZ$2405/nighttotal: NZ$4810 (2 )
2 Bedroom Suite In Islamorada! Swimming Pool, Kitchenette, Pets Allowed!
2 2
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.
Islamorada, FL
23/07 – 26/07
NZ$499/nighttotal: NZ$1497 (3 )
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.
Best Islamorada, FL resorts with a jacuzzi
Among the 69 accommodations in Islamorada, FL, here are the 1 best resorts with a jacuzzi
9.0 2594 reviews
Islamorada, FL
28/06 – 01/07
NZ$1469/nighttotal: NZ$4407 (3 )
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 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.
Best Islamorada, FL resorts with a pool
Among the 69 accommodations in Islamorada, FL, here are the 4 best resorts with a pool
Islamorada, FL
17/10 – 26/10
NZ$7131/nighttotal: NZ$64179 (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.
9.3 3 reviews
Islamorada, FL
18/07 – 22/07
NZ$855/nighttotal: NZ$3420 (4 )
2 Comfortable Units, Onsite Pool, Pets Allowed
2 4
resort , Islamorada, Village of Islands
This Islamorada apartment complex, situated on a private beach, offers easy walking access to the Theatre of the Sea and is close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks. Two 290 sq ft (approx. 27 sq m) units, each sleeping up to eight guests, feature two bedrooms, two bathrooms, a swimming pool, fitness centre, parking, and daily housekeeping, plus kayaks, paddleboards and bike rentals are available on-site.
Islamorada, FL
23/07 – 26/07
NZ$499/nighttotal: NZ$1497 (3 )
Strong Waves At Harry Harris Beach! Marina, Pool!
1 2
resort , Islamorada, Village of Islands
This resort offers private beach access in Islamorada, Village of Islands, a short 500-meter walk from the Theater of the Sea and close to Windley Key Fossil Reef Geological State Park. The "Strong Waves At Harry Harris Beach! Marina, Pool!" offer includes 335 sq. ft. rooms for two guests with air conditioning, Wi-Fi, a swimming pool, and on-site parking, with pets welcome.
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.
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 (EYW) and drive about an hour and a half, or fly into Miami International Airport (MIA) and drive about four hours. If you're driving, you'll be taking the Overseas Highway (US 1), which is a scenic drive with plenty of stops along the way.
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 and September to October. The weather is still pleasant, the crowds are smaller, and the prices are often lower.
What are the best resorts with jacuzzi in Islamorada, FL?
From Islamorada, you can easily take day trips to nearby destinations. Key West is a popular choice, known for its vibrant nightlife and historic architecture. You can also visit Dry Tortugas National Park, a remote island with a 19th-century fort and stunning coral reefs. For a more laid-back day, head to Marathon, a charming town with a variety of restaurants and shops.
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. Take a sunset cruise on a sailboat or catamaran, enjoy a private picnic on Anne's Beach, or go kayaking at Indian Key Historic State Park. You can also indulge in a couples massage at one of the many spas in the area.
What are the best pet friendly resorts in Islamorada, FL?
What are the nearest cities to explore when you are in Islamorada, FL?
Islamorada is located in the heart of the Florida Keys, so you'll be close to a variety of cities. Key West is about an hour and a half drive south, while Marathon is about 30 minutes north. If you're looking for a bigger city, Miami is about a four-hour drive.
What are the most requested amenities in resorts in Islamorada, FL?
Resorts in Islamorada are known for their beautiful beaches, so you'll find many offer private beach access, swimming pools, and water sports like kayaking and paddleboarding. Other popular amenities include restaurants, bars, and spas.
Destinations nearby
Best Islamorada, FL resorts with air conditioning
Islamorada, FL
16/10 – 18/10
NZ$1832/nighttotal: NZ$3664 (2 )
4 Spacious Units! Free Parking, Pets Allowed
4 12
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.
Islamorada, FL
28/06 – 01/07
NZ$705/nighttotal: NZ$2115 (3 )
2 Pet-friendly Units, Free Breakfast, Pool
2 5
resort , Islamorada, Village of Islands
This resort offers two-bedroom, two-bathroom holiday accommodation for eight guests, situated on a private beach in Islamorada, Village of Islands, a short walk from the Theater of the Sea and near Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. Enjoy the "2 Pet-friendly Units, Free Breakfast, Pool" offer, which includes access to a heated outdoor swimming pool, complimentary toiletries, and on-site parking, with pet-friendly options available for an additional charge, whilst being close to coral reef snorkelling and scuba diving.
9.2 2444 reviews
Islamorada, FL
23/07 – 26/07
NZ$618/nighttotal: NZ$1854 (3 )
Pines & Palms Resort
1 2
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
09/08 – 14/08
NZ$1902/nighttotal: NZ$9510 (5 )
Two Bedrooms Suite W/ocean View, Pool, Free Parking & Pet Friendly
2 2
resort , Islamorada, Village of Islands
This pet-friendly beachside apartment, offering the 'Two Bedrooms Suite W/ocean View, Pool, Free Parking & Pet Friendly', is situated in Islamorada's Matecumbe district, close to parks and easily accessible to the Morada Way Arts & Cultural District and Keys History & Discovery Centre. The two-bedroom suite boasts an ocean view, private balcony, and accommodates up to eight guests, with amenities including Wi-Fi, a pool, and proximity to water sports such as jet skiing and scuba diving at Bud n' Mary's Dive Center.
Best Islamorada, FL resorts with a gym
8.3 758 reviews
Islamorada, FL
16/10 – 18/10
NZ$3790/nighttotal: NZ$7580 (2 )
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
3 12
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.
9.0 4004 reviews
Islamorada, FL
30/07 – 06/08
NZ$580/nighttotal: NZ$4060 (7 )
Islander Resort
1 2
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.
8.8 873 reviews
Islamorada, FL
02/07 – 05/07
NZ$1428/nighttotal: NZ$4284 (3 )
Bayside Villas By Islander Resort
1 5
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.