This Keys-style detached house in Delray Beach offers direct ocean-access canal frontage with a private dock, ideal for boating and fishing enthusiasts exploring the waterfront. This family-friendly property accommodates ten guests across three bedrooms and three bathrooms, featuring an expansive outdoor living space with a heated pool, a fully equipped kitchen, and high-speed Gigabit Wi-Fi.
Islamorada, FL
03/07 – 10/07
SG$5291/nighttotal: SG$37037 (7 )
Private Beach / Heated Pool / Volleyball / Orchid
4 8
apartment , Islamorada, Village of Islands
This private tropical villa on Orchid Beach Key in Islamorada, Village of Islands, offers direct access to an expansive private beach with sweeping ocean views. This four-bedroom, four-bathroom residence accommodates up to eight guests and features a heated infinity pool, hot tub, private dock, tiki bar, and Gigabit Wi-Fi, with optional provisioning and private chef services available.
9.4 18 reviews
Islamorada, FL
08/09 – 06/10
SG$177/nighttotal: SG$4956 (28 )
Exec Bay W/heated Pool, Marina, Beach, Pets Ok, Tennis/pickleball
3 4
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.
9.6 66 reviews
Islamorada, FL
02/07 – 05/07
SG$596/nighttotal: SG$1788 (3 )
Oceanfront Condo Ocean Pointe Suites. Swimming Pool, Beach.
2 5
apartment , Tavernier
This waterfront condominium in Tavernier, Ocean Pointe, is situated at Mile Marker 91 on the ocean side, offering convenient access to John Pennekamp Coral Reef State Park and Windley Key Fossil Reef Geological State Park, just a short drive away. This recently remodelled two-bedroom, two-bathroom apartment, covering 77 square metres and accommodating up to five guests, features oceanfront views, a fully equipped kitchen, in-unit laundry, complimentary Wi-Fi, and access to a shared swimming pool and jacuzzi within a gated resort complex.
Islamorada, FL
20/06 – 27/06
SG$373/nighttotal: SG$2611 (7 )
51 M² Condo ∙ 1 Bedroom ∙ 4 Guests
1 2
apartment , Islamorada, Village of Islands
This first-floor apartment, Bayside, offers prime waterfront accommodation on Florida Bay in Islamorada, Village of Islands, a 145-kilometre drive from Miami International Airport, situated within a resort's native hammock. This 51 square metre flat, accommodating up to four guests, features one bedroom and two bathrooms, a modern kitchen with a full suite of appliances, air conditioning, Wi-Fi, a swimming pool, Jacuzzi, and direct marina access with dockage, plus admission to Islamorada Founders Park.
9.2 10 reviews
Islamorada, FL
09/10 – 12/10
SG$501/nighttotal: SG$1503 (3 )
Islamorada Paradise Overlooking The Fabulous Florida Bay.
3 2
apartment , Islamorada, Village of Islands
This Islamorada apartment, near Florida Bay, is conveniently located 5.1 km from Windley Key and 10.5 km from Upper Matecumbe Key. The 93 square metre property boasts three bedrooms, two bathrooms, sleeping six guests, and features an equipped kitchen, terrace, swimming pool, tennis court, and free Wi-Fi.
10 38 reviews
Islamorada, FL
03/07 – 05/07
SG$929/nighttotal: SG$1858 (2 )
Serene Oceanfront Keys Condo
2 5
apartment , Tavernier
This oceanfront apartment in Tavernier, Florida, offers direct access to the Ocean Pointe resort and is conveniently located near John Pennekamp Coral Reef State Park and Indian Key Historic State Park, though precise distances aren't provided. The two-bedroom, two-bathroom property sleeps six, features a king-size bed in each bedroom, a sleeper sofa, full kitchen with dishwasher, and access to resort amenities including a heated pool, hot tub, marina, tennis courts, and a private beach.
Islamorada, FL
25/07 – 01/08
SG$325/nighttotal: SG$2275 (7 )
2br 1.5bath Condo In Islamorada
1 5
apartment , Islamorada, Village of Islands
This Islamorada condo, registered as Village of Islamorada Vacation rental #25-0235, is conveniently located 0.8 kilometres from Founders Park, offering easy access to local restaurants and the beach. The two-bedroom, one-and-a-half-bathroom apartment sleeps six, includes a kitchen, swimming pool, fitness centre, parking and private marina access for observing marine life, plus numerous other amenities.
Islamorada, FL
28/06 – 01/07
SG$527/nighttotal: SG$1581 (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.
10 1 review
Islamorada, FL
30/07 – 06/08
SG$493/nighttotal: SG$3451 (7 )
Ocean Front Townhouse With Breathtaking Views!
1 2
apartment , Islamorada, Village of Islands
This oceanfront townhouse in Islamorada, Village of Islands, boasts direct beach access and is conveniently located near local restaurants and water activities, though precise distances aren't specified. Sleeping seven comfortably, this two-bedroom, one-bathroom property features a king-size bed, daybed, and pull-out sofa, a fully equipped kitchen, and access to a gated community with a heated pool and fishing pier; towels and linens are provided.
8.8 8 reviews
Islamorada, FL
09/10 – 12/10
SG$387/nighttotal: SG$1161 (3 )
Snorkeling & Kayaking Beach Resort! Seaside Villa W/patio! Marina, Pool, Parking
1 2
apartment , Islamorada, Village of Islands
This 'Snorkeling & Kayaking Beach Resort! Seaside Villa W\/patio! Marina, Pool, Parking' is located in Islamorada, just a short walk from Florida Keys Brewing Co. and Bud n' Mary's Dive Center, offering a convenient location to explore the area. The resort is situated right on the beach, giving guests direct access to the beautiful Florida Keys waters. The one-bedroom villa offers a comfortable 28 square metres of space and can accommodate up to four guests. The resort provides a range of amenities, including a heated pool with ocean views, a private beach, access to kayaks and paddleboards, and a continental breakfast each morning.
9.6 43 reviews
Islamorada, FL
18/07 – 22/07
SG$601/nighttotal: SG$2404 (4 )
Keys Comfort: 1br Condo With Den, Kitchen & Beach Access
1 4
apartment , Islamorada, Village of Islands
This smoke-free apartment is situated in Lower Matecumbe Beach, a short 4.3 kilometre walk from Sunset Drive Beach and Anne's Beach, with San Pedro Underwater Archaeological Preserve State Park being 4.3 kilometres away. The property has received excellent user ratings, making it a popular choice for travellers. This apartment features one bedroom and can accommodate up to three guests. Amenities include a fully equipped kitchen, two bathrooms, a washing machine, free Wi-Fi, a private balcony, parking, games, a library of books, and a swimming pool.
Best Islamorada, FL lodgings with a pool
Among the 1677 accommodations in Islamorada, FL, here are the 4 best ones with a pool
10 148 reviews
Islamorada, FL
17/10 – 26/10
SG$467/nighttotal: SG$4203 (9 )
Beautiful Island Home In Anglers Reef! Ocean Front Community. Pool & Boat Slip.
2 6
apartment , Islamorada, Village of Islands
This boat is situated in the exclusive gated community of Anglers Reef, located at Mile Marker 85 in Islamorada, just a short distance from the beach, Florida Keys Brewing Co., and Florida Keys Dive Center. The boat has been rated excellent by previous guests and offers a private and secure environment for travellers. The boat features two bedrooms and three bathrooms, comfortably accommodating up to six guests. It includes a range of amenities, such as a fully equipped kitchen, air conditioning, a swimming pool, a terrace, a garden, a spa, parking, and complimentary paddleboards and kayaks for exploring the nearby sandbar, fishing, or investigating the mangrove shoreline.
Islamorada, FL
08/09 – 06/10
SG$160/nighttotal: SG$4480 (28 )
Bliss On The Beach!
1 4
house , Islamorada, Village of Islands
This Islamorada holiday home, in a gated community offering easy access to the village's attractions, provides direct water access and stunning sunset views. The two-bedroom, two-bathroom property sleeps four, boasts a private dock, a shared swimming pool and clubhouse, and requires a minimum 28-day stay.
Islamorada, FL
18/07 – 22/07
SG$728/nighttotal: SG$2912 (4 )
Better Choice For Your Vacation! 2 Pet-friendly Units, Free Breakfast, Pool
2 4
apartment , Islamorada, Village of Islands
This Islamorada, Florida Keys apartment rental is conveniently located near Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park, offering easy access to local attractions. The 50 square metre self-catering property features two bedrooms, two bathrooms, sleeps eight guests, and includes amenities such as a swimming pool, free parking, and access to kayaks and paddleboards.
9.0 96 reviews
Islamorada, FL
18/07 – 22/07
SG$467/nighttotal: SG$1868 (4 )
Luxurious 2br Beachfront Condo | Steps To Pool & Ocean | Ocean Pointe Resort
2 4
apartment , Tavernier
This two-bedroom apartment in Tavernier is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to Tavernier's laid-back charm. The apartment has received excellent user and location ratings and a very good cleanliness rating. The apartment comfortably accommodates up to six guests and features a fully equipped kitchen, two bathrooms, a washing machine, and a coffee/tea maker. Enjoy relaxing amenities like a TV, internet access, and a terrace/balcony, as well as the convenience of parking and an elevator.
Best family friendly Islamorada, FL lodging
Among the 1677 accommodations in Islamorada, FL, here are the 4 best for families
Islamorada, FL
03/07 – 10/07
SG$1653/nighttotal: SG$11571 (7 )
House ∙ 4 Bedrooms ∙ 8 Guests
4 8
house , Islamorada, Village of Islands
This oceanfront villa is located in Islamorada's Arts and Culture District, approximately 145 kilometres from Miami, with bay access suitable for seaplanes. This family-friendly residence accommodates eight guests across four bedrooms and four bathrooms, boasting a 26-metre lagoon-style pool, a private 49-metre white sand beach, and an 86-metre day dock with the potential for a 10-metre boat slip.
9.6 109 reviews
Islamorada, FL
09/07 – 12/07
SG$653/nighttotal: SG$1959 (3 )
4409 Ocean Pointe Suites
2 5
apartment , Tavernier
This Tavernier beach apartment is conveniently located within a 15-minute walk of Baker's Cay Resort Beach and Harry Harris Park, offering a peaceful escape from the hustle and bustle. It has received excellent user ratings, making it a popular choice for travellers. The two-bedroom property can accommodate up to six guests and features a fully equipped kitchen, a balcony, and a swimming pool. The property also offers a range of amenities, including a tennis court, a garden, and a jacuzzi, perfect for a relaxing and enjoyable stay.
9.0 4004 reviews
Islamorada, FL
07/07 – 11/07
SG$3589/nighttotal: SG$14356 (4 )
Islander Resort
4 14
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.
9.7 41 reviews
Islamorada, FL
17/10 – 26/10
SG$479/nighttotal: SG$4311 (9 )
Anglers Reef Is Oceanfront, Blue Marlin House2/2.5
2 6
apartment , Islamorada, Village of Islands
The Blue Marlin house, a Key West-style property in Islamorada's Anglers Reef neighbourhood, is situated approximately 0.03 kilometres from an oceanfront pool and dock (fee applies). This two-bedroom, two-bathroom villa sleeps six guests and offers a fully equipped kitchen, air conditioning, a private garden, swimming pool access, complimentary paddleboards and kayaks, and proximity to a second, rentable house ideal for larger groups.
Frequently asked questions about accommodations in Islamorada, FL
What outdoor activities can visitors enjoy in and around Islamorada, FL?
Islamorada is a paradise for outdoor enthusiasts. You can go fishing, kayaking, paddleboarding, diving, snorkeling, and boating. There are also plenty of hiking and biking trails in the area. You can even rent a jet ski or go parasailing.
What are the best accommodations in Islamorada, FL?
When is the ideal time to plan a trip to Islamorada, FL?
The best time to visit Islamorada is during the spring or fall, when the weather is pleasant and the crowds are smaller. The summer months can be hot and humid, and the winter months can be cool and windy.
What are the best accommodations with a pool in Islamorada, FL?
What nearby towns or cities can be explored from Islamorada, FL?
Key Largo is just a short drive away, and it's a great place to visit the John Pennekamp Coral Reef State Park. You can also take a day trip to Key West, which is about 160km south of Islamorada.
What are the best accommodations with a jacuzzi in Islamorada, FL?
What amenities can travelers expect from accommodations in Islamorada, FL?
There are a variety of accommodations in Islamorada, from budget-friendly motels to luxury resorts. Many accommodations offer amenities like swimming pools, hot tubs, restaurants, bars, and fitness centres. You can also find accommodations with waterfront views.
What are the best accommodations for families and kids in Islamorada, FL?
Bayberry Key: Waterfront Htd Pool, Free Boat Dockage Sep-oct Only!
3 6
house , Islamorada, Village of Islands
This Islamorada villa is conveniently located within a 1.6km walk of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, with the History of Diving Museum a short 2.4km distance away. This 156 square metre, three-bedroom property sleeps six guests and boasts a private pool, spa, fully equipped kitchen, and free Wi-Fi, alongside concierge services.
9.8 183 reviews
Islamorada, FL
18/07 – 22/07
SG$574/nighttotal: SG$2296 (4 )
Family Fun Oceanside! Condo With Pool + Beach
2 4
apartment , Tavernier
This family-friendly apartment is located in Tavernier, a short 5 kilometre walk from Baker's Cay Resort Beach and Harry Harris Park, with Mariners Hospital and Florida Keys Dive Center within a 5 kilometre radius. The accommodation has excellent user, location and cleanliness ratings. The apartment has 2 bedrooms and 2 bathrooms spread over 84 square metres and can comfortably accommodate up to 4 guests. Amenities include a fully equipped kitchen, a washing machine, free Wi-Fi, a swimming pool, a jacuzzi, a terrace, a garden, a spa, a tennis court, and parking.
This Islamorada holiday home is situated on the beach, just a few kilometres from Windley Key Fossil Reef Geological State Park, Founders Park, and Rain Barrel Village. The property is highly rated, with guests consistently praising its excellent location and amenities. This two-bedroom property can accommodate up to six guests and features a fully equipped kitchen, air conditioning, a swimming pool, and a terrace. Guests can enjoy direct beach access, a garden, a spa, and parking, as well as a range of activities including fishing, snorkeling, diving, and boating.
Islamorada, FL
08/09 – 06/10
SG$296/nighttotal: SG$8288 (28 )
Beacon Reef 501
2 4
house , Islamorada, Village of Islands
Beacon Reef 501 is a beachfront villa in Islamorada, Village of Islands, situated 2.1 kilometres from the Theater of the Sea and 2.4 kilometres from Upper Matecumbe Key. This two-bedroom villa accommodates up to seven guests and features a jacuzzi, spa, fitness centre, water park access, and complimentary WiFi, with sea views from the terrace.
Best Islamorada, FL accommodations with a kitchen
9.9 285 reviews
Islamorada, FL
28/06 – 01/07
SG$464/nighttotal: SG$1392 (3 )
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
2 5
apartment , Tavernier
This oceanfront apartment is located in Tavernier at mile marker 92, within the gated resort community of Ocean Pointe, directly across from the pool, and is within walking distance of a small grocery store, a restaurant/bar, and a gas station. The apartment has consistently received excellent ratings for its location, cleanliness, and overall user experience. The accommodation offers 79 square metres of living space, comfortably sleeping up to 6 guests in its two bedrooms and two bathrooms. Guests can enjoy a range of on-site amenities, including a swimming pool, a Jacuzzi, a terrace, a garden, a fitness centre, and parking, alongside direct ocean views, a fully equipped kitchen, and access to a boat ramp and marina.
9.6 4 reviews
Islamorada, FL
02/07 – 05/07
SG$585/nighttotal: SG$1755 (3 )
2br Condo W/ Ocean View, Pool & Tropical Setting
2 5
apartment , Tavernier
This Tavernier oceanfront apartment, near Key Largo and Islamorada, offers private beach access and is conveniently located for exploring John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre. The 79 square metre (850 square foot) property sleeps six guests in two bedrooms and two bathrooms, boasting a fully equipped kitchen, swimming pool, parking, and internet access; kayaking and motor boating opportunities are also nearby.
8.8 10 reviews
Islamorada, FL
03/07 – 05/07
SG$920/nighttotal: SG$1840 (2 )
Ocean Pointe 2309
2 5
house , Tavernier
Ocean Pointe 2309, a beachfront property in Tavernier, Florida, offers ocean views and is a 14-minute walk from Harry Harris Park Beach and 4.8km from Pigeon Key. This two-bedroom, two-bathroom house boasts 85 square metres of floor space, sleeps up to 11 guests, and includes a private pool, bar, free Wi-Fi, and parking.
8.8 3 reviews
Islamorada, FL
03/07 – 05/07
SG$711/nighttotal: SG$1422 (2 )
Key Largo 2br - Partial Ocean Views, Pool & Beach
2 5
apartment , Tavernier
This Tavernier oceanfront condo, near Key Largo and Islamorada, offers direct beach access and proximity to John Pennekamp Coral Reef State Park and Jacob's Aquatic Centre. The 79 square metre (850 square foot) apartment sleeps six, featuring two bedrooms, two bathrooms, a fully equipped kitchen (fridge, microwave, dishwasher), air conditioning, a swimming pool, parking, and internet access; resort amenities include a junior Olympic-sized swimming pool, hot tub, and tennis courts.