Best Holiday rentals and Airbnb offers in Islamorada, FL
9.0 1 review
Islamorada, FL
07/08 – 23/08
SG$405/nighttotal: SG$6480 (16 )
Whispering Palms Sea Gulls 210
2 4
house , Islamorada, Village of Islands
Whispering Palms Sea Gulls 210, a two-bedroom property in Key Largo, is situated approximately 8.5 km from both Windley Key and Pigeon Key. This Islamorada holiday home boasts 110 square metres of living space, sleeping up to six guests and offering a private patio with sea views, a swimming pool, fitness centre, and fully equipped kitchen.
10 25 reviews
Islamorada, FL
07/08 – 23/08
SG$683/nighttotal: SG$10928 (16 )
Pristine Pool Front Home W/ocean Views Anglers 148
1 4
apartment , Islamorada, Village of Islands
This Islamorada townhouse, situated in the Village of Islands, offers ocean views and is approximately 5km from Alligator Reef, a renowned snorkelling and diving spot. The two-bedroom, two-bathroom property sleeps seven, features a fully equipped kitchen with Viking appliances, two spacious decks, a private washer/dryer, and access to kayaks and a resort-style swimming pool.
9.3 125 reviews
Islamorada, FL
28/06 – 01/07
SG$496/nighttotal: SG$1488 (3 )
Oceanfront Views At Ocean Pointe + Pool + Beach & Marina Access, Updated 2br
2 5
apartment , Tavernier
This apartment in Tavernier is ideally located just a short walk from Baker's Cay Resort Beach and Harry Harris Park, with other attractions like Mariners Hospital and Florida Keys Dive Center within a 5km radius. The apartment enjoys excellent user, location, and cleanliness ratings, guaranteeing a comfortable and enjoyable stay. The spacious apartment, measuring 78 square metres, comfortably accommodates up to 6 guests across two bedrooms and two bathrooms. Guests can enjoy a range of amenities including a private pool and spa tub, a fully equipped kitchen, air conditioning, and a balcony perfect for relaxing and enjoying the Tavernier weather.
9.1 3677 reviews
Islamorada, FL
07/07 – 11/07
SG$1010/nighttotal: SG$4040 (4 )
Cheeca Lodge & Spa
2 4
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.
Islamorada, FL
26/06 – 30/06
SG$535/nighttotal: SG$2140 (4 )
Florida Keys Boat Trips Multi Activity
1 3
boat , Islamorada, Village of Islands
This Islamorada boat rental, located a short walk from Windley Key and 0.8km from Windley Key Fossil Reef Geological State Park, offers easy access to local attractions. Sleeping up to 11 guests in one bedroom and one bathroom, this vessel boasts private beach access, proximity to Theater of the Sea (2.3km), and allows pets.
Islamorada, FL
30/07 – 06/08
SG$391/nighttotal: SG$2737 (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.
8.0 4 reviews
Islamorada, FL
07/07 – 11/07
SG$524/nighttotal: SG$2096 (4 )
Ideal Location! Pets Allowed, Onsite Pool
2 4
resort , Islamorada, Village of Islands
This resort in Islamorada, Village of Islands, is located approximately 160 kilometres south of Miami, offering a prime spot for fishing, boating, and enjoying local cuisine with bay and ocean vistas. This pet-friendly hotel, offering the "Ideal Location! Pets Allowed, Onsite Pool" package, provides 2-bedroom accommodation for up to four guests, featuring air conditioning, internet, a swimming pool, and daily cleaning services within its 51.5 square metre rooms.
9.8 18 reviews
Islamorada, FL
01/01 – 31/05
SG$340/nighttotal: SG$51000 (150 )
Capt Craig's 2 Bedroom/1 Bath Apartment In Tavernier, Florida Keys
2 2
apartment , Islamorada, Village of Islands
This Islamorada apartment rental, located in Plantation Key Colony, Tavernier, is approximately 1.5 hours (241km) from Miami International Airport and near Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park. The two-bedroom, one-bathroom property sleeps six guests and offers air conditioning, internet access, and is pet-friendly; nearby activities include diving at the Florida Keys Dive Center and exploring Jacob's Aquatic Center.
9.6 18 reviews
Islamorada, FL
04/08 – 09/08
SG$603/nighttotal: SG$3015 (5 )
Double The Views: Florida Keys 1br With 2 Balconies & Pool Access
1 5
apartment , Islamorada, Village of Islands
This one-bedroom condo is located in Lower Matecumbe Beach, a short 10-minute walk from Sunset Drive Beach and Anne's Beach, and a 4.3 km drive from the San Pedro Underwater Archaeological Preserve State Park. The property has received excellent user ratings and is a popular choice for travellers seeking a relaxing and convenient stay. The 74 square metre apartment comfortably accommodates up to 6 guests and features a fully equipped kitchen, two bathrooms, a washing machine, free Wi-Fi, a balcony, games, and books. Guests can enjoy the convenience of self-catering, relax in the private outdoor space, and explore the nearby beaches and attractions.
Islamorada, FL
08/09 – 06/10
SG$308/nighttotal: SG$8624 (28 )
House ∙ 3 Bedrooms ∙ 5 Guests
3 2
house , Islamorada, Village of Islands
This bayside villa in Islamorada, Village of Islands, offers a private retreat within 1 kilometre of the Publix Shopping Centre and downtown amenities, ideal for those seeking a tranquil escape with convenient access to local attractions. This three-bedroom, two-bathroom holiday home accommodates up to five guests and features a private heated and chilled swimming pool, a spacious garden with mature trees, and ample parking, including space for a boat trailer, making it perfect for fishing and boating enthusiasts.
9.7 26 reviews
Islamorada, FL
08/09 – 06/10
SG$227/nighttotal: SG$6356 (28 )
Islamorada Getaway Townhouse
1 2
house , Islamorada, Village of Islands
This Islamorada townhouse, situated in the Village of Islands, is centrally located, minutes (less than 1.6km) from the Islamorada sandbar and acclaimed restaurants. The three-bedroom, two-bathroom property sleeps eight guests and boasts a fully equipped kitchen, private swimming pool, garden, and parking; note the spiral staircase.
This one-bedroom flat is located in the centre of Islamorada, directly on a private beach with ocean views and within 1.5 kilometres of Islamorada Brewery & Distillery and Florida Keys Brewing Co. This pet-friendly accommodation offers a heated outdoor swimming pool, complimentary Wi-Fi, and on-site bike, kayak, and paddleboard rentals, with a capacity for four guests.
Best family friendly Islamorada, FL holiday rentals
Among the 1414 accommodations in Islamorada, FL, here are the 4 best family friendly rentals
10 1 review
Islamorada, FL
01/01 – 31/05
SG$612/nighttotal: SG$91800 (150 )
Paradise Retreat
3 2
apartment , Islamorada, Village of Islands
This Islamorada holiday home is situated near Sunset Drive Beach (0.6 km), Anne's Beach (4.8 km), and Robbie's of Islamorada (9.7 km), offering easy access to local attractions. The three-bedroom, three-bathroom property sleeps eight guests and boasts a fully equipped kitchen, Wi-Fi, a private garden, spa, and barbecue facilities; pets are welcome.
10 4 reviews
Islamorada, FL
10/07 – 15/07
SG$2956/nighttotal: SG$14780 (5 )
4 Bedroom Oceanfront Accessible Villa – Capacity 8
4 6
house , Islamorada, Village of Islands
This Islamorada waterfront villa, offering direct beach access, is situated in the Village of Islands and is conveniently located near various attractions within Islamorada (precise distances unspecified). The four-bedroom, four-bathroom property sleeps eight guests and boasts a private marina (size restrictions apply, no boat ramp or jet ski/trailer parking), multiple pools, a jacuzzi, fitness pavilion, watersports equipment rentals, and on-site spa services.
Islamorada, FL
08/09 – 06/10
SG$296/nighttotal: SG$8288 (28 )
153 M² House ∙ 3 Bedrooms ∙ 6 Guests
3 2
house , Islamorada, Village of Islands
This three-bedroom, three-bathroom townhome is located within the exclusive gated Executive Bay Club in Islamorada, Florida, directly adjacent to Founder's Park, offering privacy and security with stunning ocean views. Spanning 153 square meters, this family-friendly residence accommodates up to six guests and features a newly remodelled interior, a private on-site beach, a freshwater swimming pool, tennis and pickleball courts, and marina access for daytime use.
10 158 reviews
Islamorada, FL
27/06 – 04/07
SG$539/nighttotal: SG$3773 (7 )
Aquamarine Oceanview+special Rates+\ndock+pool+gym+spa+1535 Star Reviews!!!
2 2
apartment , Islamorada, Village of Islands
This waterfront apartment is situated in Islamorada's Matecumbe district, just a short distance from Bud n' Mary's Dive Center and Florida Keys Brewing Co., offering stunning views of the ocean and marina. The apartment has received excellent user ratings, indicating a high level of satisfaction among previous guests. The apartment is spacious, measuring 158 square metres and accommodating up to 6 guests. It features a range of amenities and activities, including a private dock, a heated pool, a hot tub, a fitness centre, lighted tennis courts, a clubhouse, and a well-equipped equipment closet.
Best Islamorada, FL holiday rentals with a pool
Among the 1414 accommodations in Islamorada, FL, here are the 4 best rentals with a pool
9.7 28 reviews
Islamorada, FL
07/08 – 23/08
SG$430/nighttotal: SG$6880 (16 )
Islamorada Bungalow #5
1 4
apartment , Islamorada, Village of Islands
This Islamorada bungalow, ideally situated near pristine beaches and world-class fishing opportunities in the Village of Islands, offers easy access to various attractions. The two-bedroom, one-bathroom house sleeps four, boasting a fully equipped kitchen, in-unit laundry, a private porch, and access to a community heated swimming pool; on-site bicycles are available for exploring the area.
9.7 228 reviews
Islamorada, FL
04/08 – 09/08
SG$538/nighttotal: SG$2690 (5 )
Keys Waterfront Condo: Beach, Pool & Sunset Views!
2 5
apartment , Tavernier
This waterfront apartment in Tavernier is located a short 2.4 km walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful waters and the local area. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment spans 84 square metres and comfortably accommodates up to 6 guests, with 2 bedrooms and 2 bathrooms. You'll enjoy a range of amenities including a swimming pool, jacuzzi, terrace, garden, spa, tennis court, and parking, as well as a fully equipped kitchen and air conditioning.
Islamorada, FL
28/06 – 01/07
SG$660/nighttotal: SG$1980 (3 )
Better Choice For Your Vacation! 2 Pet-friendly Units, Free Breakfast, Pool
2 5
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.
10 8 reviews
Islamorada, FL
27/06 – 04/07
SG$731/nighttotal: SG$5117 (7 )
Fl Keys Ocean Front Escape
1 2
apartment , Islamorada, Village of Islands
This oceanfront apartment in Islamorada, Village of Islands, offers direct sea access and is located within 500 meters of the oceanfront beach. This two-bedroom, three-bathroom property accommodates four guests and features a private rooftop deck, a new 10-meter boat dock, a heated community pool, and on-site peacock viewing.
Frequently asked questions about holiday rentals in Islamorada, FL
What are some interesting places to visit in or near Islamorada, FL?
You've got to check out the Florida Keys Aquarium Encounters in Islamorada, it's a great place to see local marine life. If you're looking for something a bit more adventurous, the Theater of the Sea in Marathon is just a short drive away, where you can see dolphins, sea lions, and even sharks up close. And of course, no trip to Islamorada is complete without a visit to the Anne's Beach in Islamorada, a beautiful white sand beach perfect for relaxing and soaking up the sun.
What are the best Airbnb and vacation rentals in Islamorada, FL?
Which walking or cycling routes are the best in Islamorada, FL?
The Islamorada Founders Park is a great spot for a leisurely stroll or bike ride, with scenic views of the water. If you're looking for something more challenging, the Overseas Highway offers stunning views of the ocean and is a popular route for cycling. Just be sure to be mindful of traffic, especially during peak season.
What are the most popular Airbnbs in Islamorada, FL?
What sports or outdoor activites can visitors enjoy in and around Islamorada, FL?
Islamorada is a paradise for water sports enthusiasts. You can go fishing, snorkelling, diving, kayaking, paddleboarding, or even jet skiing. If you're looking for something a bit more laid-back, you can always go for a swim or just relax on the beach. There's also plenty of hiking and biking trails in the area.
What are the best vacation rentals with a pool in Islamorada, FL?
What other towns or cities can be easily accessed from Islamorada, FL?
Islamorada is a great base for exploring the Florida Keys. You can easily reach Key Largo, Marathon, and Key West by car. Each town has its own unique charm and offers a variety of attractions and activities.
What are the best rentals for families and kids in Islamorada, FL?
What amenities are commonly available in vacation rentals in Islamorada, FL?
Most vacation rentals in Islamorada come equipped with basic amenities like a kitchen, bathroom, and laundry facilities. Many also offer additional features like a private pool, hot tub, or even a boat dock. You can find rentals with everything from a simple studio to a luxurious villa, depending on your budget and preferences.
What are the best rentals or Airbnbs with a jacuzzi in Islamorada, FL?
What time of year is best to rent a vacation rental Islamorada, FL?
The best time to visit Islamorada is during the shoulder seasons, from April to June and September to November, when the weather is still pleasant and the crowds are smaller. The summer months can be hot and humid, and the winter months can be crowded and expensive.
Destinations nearby
Best Islamorada, FL holiday rentals with a balcony
10 2 reviews
Islamorada, FL
08/09 – 06/10
SG$1220/nighttotal: SG$34160 (28 )
246 M² House ∙ 4 Bedrooms ∙ 8 Guests
4 2
house , Islamorada, Village of Islands
This newly built villa is located in Islamorada, Village of Islands, on a quiet ocean-side street between Cheeca Lodge Resort and Caribbean Resort, offering a private luxury getaway. This 246 square meter residence accommodates up to 8 guests with 4 en-suite bedrooms, featuring a private saltwater pool, outdoor kitchen, smart TVs, and complimentary passes to The Islander Resort and discounted access to Founders Park.
This Matecumbe holiday home in Islamorada, Village of Islands, is situated within 3.2km of San Pedro Underwater Archaeological Preserve State Park, Robbie's of Islamorada, and Indian Key Historic State Park, and 3.7km from Sunset Drive Beach. The 49-square-metre property offers two bedrooms, one bathroom, sleeps four guests, and boasts a private pool, jacuzzi, spa, and fully equipped kitchen including a dishwasher; concierge services are also available.
8.9 56 reviews
Islamorada, FL
07/07 – 11/07
SG$402/nighttotal: SG$1608 (4 )
Welcome To The Pelican Lodge !
2 4
apartment , Tavernier
This beachfront Tavernier apartment offers direct private beach access, a 2.6km walk from Harry Harris Park Beach and a 4.8km drive from Pigeon Key. The two-bedroom, two-bathroom flat sleeps eleven guests and boasts a fully equipped kitchen, swimming pool, jacuzzi, tennis court, bar, free Wi-Fi, and sea views from its terrace.
10 2 reviews
Islamorada, FL
03/08 – 05/08
SG$410/nighttotal: SG$820 (2 )
Beach Retreat 2 Bedroom Ocean View, Pool & Beach
2 5
apartment , Tavernier
This Tavernier oceanfront apartment, near Key Largo and Islamorada, offers direct beach access and proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park. The 79-square-metre property features two bedrooms (sleeping up to six guests), two bathrooms, a fully equipped kitchen (including fridge, microwave, and dishwasher), and access to resort amenities such as a swimming pool, hot tub, and tennis courts.
Best Islamorada, FL holiday rentals with parking
9.6 10 reviews
Islamorada, FL
27/06 – 04/07
SG$445/nighttotal: SG$3115 (7 )
Charming Bayside 2 Bed, 2 Bath Condo At Futura In Islamorada Wifi, Pool, Dockage
2 2
apartment , Islamorada, Village of Islands
This Islamorada condominium is located in Tavernier, at mile marker 88.5 on the bay side, offering waterfront views and convenient access to the Florida Keys Dive Center, Mangrove Marina, John Pennekamp Coral Reef State Park, and Windley Key Fossil Reef Geological State Park. This fully furnished 2-bedroom condo spans 79 square metres, accommodates up to six guests, and features en-suite bathrooms, a balcony overlooking tennis courts, on-site WiFi, central air conditioning, and laundry facilities, with available dockage, a boat ramp, and trailer parking for boating enthusiasts.
9.8 490 reviews
Islamorada, FL
01/01 – 31/05
SG$605/nighttotal: SG$90750 (150 )
Fla Keys Luxury Houseboat, Prime Location-steps To Fun, Food & Water Adventures
2 2
houseboat , Islamorada, Village of Islands
This houseboat is located at Mile Marker 90, just south of Key Largo, offering easy access to the ocean and the bay via Tavernier Creek. The property has received excellent ratings from previous guests for its location, cleanliness and overall experience. The houseboat spans 111 square metres and can accommodate up to four guests. It boasts a fully equipped kitchen, a terrace, a garden, a spa, a fitness centre, and parking, as well as access to a range of activities and services at the marina.
9.8 43 reviews
Islamorada, FL
27/06 – 04/07
SG$710/nighttotal: SG$4970 (7 )
Keezy Dream House + Beach, Pool & Kayaks - Anglers Reef 119
2 2
apartment , Islamorada, Village of Islands
This waterfront property in Islamorada is located just 0.4 miles from Windley Key Fossil Reef Geological State Park and within 3 miles of Founders Park and Islamorada County Park. Guests consistently rate this property as excellent. The house has two bedrooms and can accommodate up to six guests. This family-friendly property offers a range of amenities, including a private pool, spa, a fully equipped kitchen, and a balcony with stunning views.
Islamorada, FL
07/07 – 11/07
SG$701/nighttotal: SG$2804 (4 )
Island Escape In Islamorada | Breakfast, Pool & Pet-friendly Stay!
2 4
apartment , Islamorada, Village of Islands
This two-bedroom flat is located by the sea in the Matecumbe district of Islamorada, within walking distance of the History of Diving Museum and Keys History & Discovery Centre, and a short drive from Windley Key Fossil Reef Geological State Park and Indian Key Historic State Park. This 52 square metre apartment accommodates up to four guests, offers daily cleaning, complimentary toiletries, air conditioning, Wi-Fi, a swimming pool, and pet-friendly accommodation for two dogs under 22.7 kilograms, with one parking space per unit.