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Guest favorite
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Private beach
Anglers Reef Paradise
- BBQ facilities
- Free parking
- Air conditioning
- Heating
- Pool with view
- Family rooms
Situated merely a 5-minute walk from Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise Islamorada villa offers guests to relax by a heated pool. This holiday home features opportunities for snorkelling, diving, and cycling in the area, 2.5 km from Rain Barrel Village.
Anglers Reef Paradise
- BBQ facilities
- Free parking
- Air conditioning
- Heating
- Pool with view
- Family rooms
Anglers Reef Paradise
Situated merely a 5-minute walk from Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise Islamorada villa offers guests to relax by a heated pool. This holiday home features opportunities for snorkelling, diving, and cycling in the area, 2.5 km from Rain Barrel Village.
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Private beach
Anglers Reef Vacation Rental
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Pool with view
- Family rooms
The 2-bedroom Anglers Reef Vacation Rental Islamorada villa is located within 3 km of Islamorada and provides canyoning, cycling, and fisheries for active guests.
Anglers Reef Vacation Rental
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Pool with view
- Family rooms
Anglers Reef Vacation Rental
The 2-bedroom Anglers Reef Vacation Rental Islamorada villa is located within 3 km of Islamorada and provides canyoning, cycling, and fisheries for active guests.
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Private beach
Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Family rooms
The 2-bedroom Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina hosts up to 6 guests and provides proximity to Windley Key Fossil Reef Geological State Park, situated only 0.6 km away.
An outdoor swimming pool, as well as access to a sunbathing terrace and a picnic area are available at the accommodation. While staying at Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina, you can enjoy snorkelling, diving, and canyoning.
Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Live entertainment
- Family rooms
Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina
The 2-bedroom Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina hosts up to 6 guests and provides proximity to Windley Key Fossil Reef Geological State Park, situated only 0.6 km away.
An outdoor swimming pool, as well as access to a sunbathing terrace and a picnic area are available at the accommodation. While staying at Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina, you can enjoy snorkelling, diving, and canyoning.
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Beach access
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Heated swimming pool
The 3-bedroom Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada villa is nestled merely a 9-minute walk from Lobster Trap Art Gift Shop and Gallery and can accommodate up to 6 guests.
Guests will enjoy a spacious balcony and a heated pool.
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Heated swimming pool
Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views!
The 3-bedroom Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! Islamorada villa is nestled merely a 9-minute walk from Lobster Trap Art Gift Shop and Gallery and can accommodate up to 6 guests.
Guests will enjoy a spacious balcony and a heated pool.
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Beach access
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Children's play area
Nestled approximately 15 minutes on foot from History of Diving Museum, the 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa entices guests to explore various tourist destinations nearby.
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Children's play area
Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Nestled approximately 15 minutes on foot from History of Diving Museum, the 3-bedroom Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable Islamorada villa entices guests to explore various tourist destinations nearby.
Key Lime Cottage In The Heart Of Islamorada
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Heated swimming pool
- Children's play area
Nestled a 10-minute ride from Lignumvitae Key Island, Key Lime Cottage In The Heart Of Islamorada entices guests to explore various tourist destinations nearby.
Key Lime Cottage In The Heart Of Islamorada
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Heated swimming pool
- Children's play area
Key Lime Cottage In The Heart Of Islamorada
Nestled a 10-minute ride from Lignumvitae Key Island, Key Lime Cottage In The Heart Of Islamorada entices guests to explore various tourist destinations nearby.
Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Live entertainment
- Pool with view
- Family rooms
Accommodating up to 7 guests, the 3-bedroom Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is situated around a 10-minute drive from renowned cultural sites such as Rain Barrel Sculpture Gallery.
Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Live entertainment
- Pool with view
- Family rooms
Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool
Accommodating up to 7 guests, the 3-bedroom Hooked On Islamorada Oceanfront Townhome, Private Dock, Pool villa is situated around a 10-minute drive from renowned cultural sites such as Rain Barrel Sculpture Gallery.
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Private beach
Executive Bay Islamorada By Sofla Vacations
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Family rooms
Staying at the 2-room Executive Bay Islamorada By Sofla Vacations villa, guests can visit Islamorada, which is only 250 metres away.
You can relax by an outdoor swimming pool, and use a picnic area and a golf course onsite. The surrounding area is popular for snorkelling, diving, and fisheries at the Islamorada accommodation.
Executive Bay Islamorada By Sofla Vacations
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Family rooms
Executive Bay Islamorada By Sofla Vacations
Staying at the 2-room Executive Bay Islamorada By Sofla Vacations villa, guests can visit Islamorada, which is only 250 metres away.
You can relax by an outdoor swimming pool, and use a picnic area and a golf course onsite. The surrounding area is popular for snorkelling, diving, and fisheries at the Islamorada accommodation.
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Top location
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Beach access
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Children's play area
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa enjoys a convenient location in Islamorada and offers its guests to make use of an outdoor swimming pool.
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Children's play area
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location
Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa enjoys a convenient location in Islamorada and offers its guests to make use of an outdoor swimming pool.
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Private beach
Turtle Nest Estate
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Open-air bath
- Saltwater pool
Offering a Jacuzzi for guests to unwind, Turtle Nest Estate Villa Islamorada is located nearly 5 minutes' walk from the Lower Matecumbe Key. Guests can enjoy snorkelling, diving, and fishing at this Islamorada villa, located 3.8 km from the 280-acre island "Lignumvitae Key Botanical State Park".
Turtle Nest Estate
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Open-air bath
- Saltwater pool
Turtle Nest Estate
Offering a Jacuzzi for guests to unwind, Turtle Nest Estate Villa Islamorada is located nearly 5 minutes' walk from the Lower Matecumbe Key. Guests can enjoy snorkelling, diving, and fishing at this Islamorada villa, located 3.8 km from the 280-acre island "Lignumvitae Key Botanical State Park".
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Beach access
At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Children's play area
Along with proximity to Windley Key Fossil Reef Geological State Park, only 500 metres away, the 3-bedroom At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa offers opportunities for snorkelling, ping pong, and fisheries in the area. The Islamorada holiday home hosts up to 6 guests and provides them with parking.
At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Children's play area
At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom
Along with proximity to Windley Key Fossil Reef Geological State Park, only 500 metres away, the 3-bedroom At The Sandbar - Oceanfront, Htd Pool, Dock, Gameroom Islamorada villa offers opportunities for snorkelling, ping pong, and fisheries in the area. The Islamorada holiday home hosts up to 6 guests and provides them with parking.
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Beach access
Pineapple Beach
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Golf centre
- Garden area
- Cots
Situated 2.5 km from Rain Barrel Village, Pineapple Beach Islamorada villa entices guests to explore various tourist attractions in the area. Offering cycling and fisheries, this 5-bedroom holiday home is suitable for 10 guests.
Pineapple Beach
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Golf centre
- Garden area
- Cots
Pineapple Beach
Situated 2.5 km from Rain Barrel Village, Pineapple Beach Islamorada villa entices guests to explore various tourist attractions in the area. Offering cycling and fisheries, this 5-bedroom holiday home is suitable for 10 guests.
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Beach access
Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Children's play area
Nestled 15 minutes' walk from History of Diving Museum, Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa entices guests to explore various tourist destinations nearby.
Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Children's play area
Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location
Nestled 15 minutes' walk from History of Diving Museum, Isla Key Acai - Waterfront Boutique Resort, Island Paradise, Prime Location Islamorada villa entices guests to explore various tourist destinations nearby.
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Great deal
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Beach access
Islamorada Modern Penthouse With Private Beach
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Jacuzzi
- Outdoor swimming pool
Boasting a Jacuzzi, the 3-bedroom Islamorada Modern Penthouse With Private Beach villa is located only a 9-minute walk from Lignumvitae Key Botanical State Park and can accommodate 7 guests.
Islamorada Modern Penthouse With Private Beach
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Jacuzzi
- Outdoor swimming pool
Islamorada Modern Penthouse With Private Beach
Boasting a Jacuzzi, the 3-bedroom Islamorada Modern Penthouse With Private Beach villa is located only a 9-minute walk from Lignumvitae Key Botanical State Park and can accommodate 7 guests.
Tollgate Tides
- Cookware/ Kitchen utensils
- Ironing facilities
- Tea and coffee facilities
- Patio
Tollgate Tides Villa Islamorada is located 3.1 km from the Lower Matecumbe Key and provides windsurfing and fishing for active guests. Located about 10 minutes' drive from the Craig Key, the property boasts a terrace with views of the sea.
Tollgate Tides
- Cookware/ Kitchen utensils
- Ironing facilities
- Tea and coffee facilities
- Patio
Tollgate Tides
Tollgate Tides Villa Islamorada is located 3.1 km from the Lower Matecumbe Key and provides windsurfing and fishing for active guests. Located about 10 minutes' drive from the Craig Key, the property boasts a terrace with views of the sea.
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Beach access
Sunshine Place
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Aqua park
During the stay at Sunshine Place Islamorada villa, guests can indulge in windsurfing, snorkelling, and bowling or visit Rain Barrel Sculpture Gallery, located 3.8 km away. Enticing guests with an aqua park and spa therapy, this 1-bedroom holiday home is situated 10 minutes by car from Lobster Trap Art Gift Shop and Gallery.
Sunshine Place
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Air conditioning
- Fitness centre
- Aqua park
Sunshine Place
During the stay at Sunshine Place Islamorada villa, guests can indulge in windsurfing, snorkelling, and bowling or visit Rain Barrel Sculpture Gallery, located 3.8 km away. Enticing guests with an aqua park and spa therapy, this 1-bedroom holiday home is situated 10 minutes by car from Lobster Trap Art Gift Shop and Gallery.
Are you in a hurry?
Here is a quick list of hotels in Islamorada, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Anglers Reef Paradise |
9.6 / 10 (19 Reviews) |
From 382$ | |
| Anglers Reef Vacation Rental |
9.8 / 10 (4 Reviews) |
From 365$ | |
| Anglers Reef Islamorada 2Br 3Ba Oceanview Home In Gated Community With Resort Style Pool, Private Beach And Marina |
10.0 / 10 (2 Reviews) |
From 394$ | |
| Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water Views! |
10.0 / 10 (3 Reviews) |
From 1093$ | |
| Isla Key Lime - Waterfront Boutique Resort, Htd Pool, Dock, Walkable |
10.0 / 10 (1 Reviews) |
From 590$ |
More accommodations in Islamorada
Frequently Asked Questions
Which family villas in Islamorada have pools?
Tollgate Tides and the Anglers Reef Vacation Rental feature pools that are great for families. Enjoy the refreshing water and a safe area for kids to play.
For the best pool experience, visit early in the morning to avoid peak sun hours.
What family villas in Islamorada are kid-friendly?
Key Lime Cottage and Sunshine Place offer amenities like family rooms and easier access to the beach. Your kids can enjoy water activities nearby.
Check for special family packages that include children's meals or activities.
Which family villas near the beach provide direct access?
Islamorada Modern Penthouse With Private Beach and Pineapple Beach have direct beach access for sun and fun. It's perfect for spending a whole day by the water.
Pack beach toys for the kids; it's easier to play at beaches with family-friendly amenities.
What family villas in Islamorada offer two bedrooms?
Anglers Reef Islamorada 2Br 3Ba Oceanview Home and Turtle Nest Estate both have spacious two-bedroom setups. Plenty of room for your family can make your stay comfortable.
Book ahead to secure two-bedroom options, especially during peak holiday seasons.
Which villas in Islamorada are convenient for water sports?
Isla Key Guava and Isla Key Acai provide dock access for easy boating and water sports. They are close to places offering rentals for kayaks and paddleboards.
Reserve your water sports equipment the night before for the best selection.
What family villas near popular landmarks can I find?
Executive Bay Islamorada and Anglers Reef Paradise are near the Florida Keys History Museum and many restaurants. This location keeps you close to popular attractions.
Visit the museum on weekdays for fewer crowds and a better experience.
Which family villas are budget-friendly in Islamorada?
Tollgate Tides and Executive Bay provide comfortable accommodations at reasonable prices for families. They make great options without sacrificing quality.
Try to book during the shoulder season for better rates and availability.
Are there any family-friendly events in Islamorada throughout the year?
Yes, the Islamorada Seafood Festival is held every January. It features fun activities for children, live music, and a variety of seafood delicacies.
Arrive early for the best parking and to secure a good spot for the kids' activities.
How can families travel around Islamorada easily?
Renting bikes is a popular option for families to explore the area. This way, you can visit attractions at a leisurely pace without worrying about parking.
Head to the Village of Islamorada Community Center for bike rental facilities and enjoy the laid-back paths nearby.
What safety tips should families keep in mind while visiting Islamorada?
Stick to well-lit areas and supervise children, especially at night. Always use designated crosswalks when walking along busy streets.
Avoid walking on unpaved paths after sunset to ensure a safe return to your accommodation.
Islamorada and related destinations