Holiday Rentals in Islamorada, FL

1414 available vacation rental offers

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Islamorada, FL holiday rentals
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Best Holiday rentals and Airbnb offers in Islamorada, FL

Best family friendly Islamorada, FL holiday rentals

Among the 1414 accommodations in Islamorada, FL, here are the 4 best family friendly rentals

Paradise Retreat - Islamorada, FL
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.
4 Bedroom Oceanfront Accessible Villa – Capacity 8 - Islamorada, FL
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.
153 M² House ∙ 3 Bedrooms ∙ 6 Guests - Islamorada, FL
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.
Aquamarine Oceanview+special Rates+\ndock+pool+gym+spa+1535 Star Reviews!!! - Islamorada, FL
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

Islamorada Bungalow #5 - Islamorada, FL
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.
Keys Waterfront Condo: Beach, Pool & Sunset Views! - Islamorada, FL
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.
Better Choice For Your Vacation! 2 Pet-friendly Units, Free Breakfast, Pool - Islamorada, FL
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.
Fl Keys Ocean Front Escape - Islamorada, FL
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

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Best Islamorada, FL holiday rentals with a balcony

246 M² House ∙ 4 Bedrooms ∙ 8 Guests - Islamorada, FL
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.
Islamorada Retreat "Bungalow Blue" W/ Heated Pool, Bikes, Bbq, Amenities Galore! - Islamorada, FL
10 24 reviews
Islamorada, FL
07/08 – 23/08
SG$606/nighttotal: SG$9696 (16 )

Islamorada Retreat "Bungalow Blue" W/ Heated Pool, Bikes, Bbq, Amenities Galore!

2 4
apartment , Islamorada, Village of Islands
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.
Welcome To The Pelican Lodge ! - Islamorada, FL
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.
Beach Retreat 2 Bedroom Ocean View, Pool & Beach - Islamorada, FL
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

Charming Bayside 2 Bed, 2 Bath Condo At Futura In Islamorada Wifi, Pool, Dockage - Islamorada, FL
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.
Fla Keys Luxury Houseboat, Prime Location-steps To Fun, Food & Water Adventures - Islamorada, FL
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.
Keezy Dream House + Beach, Pool & Kayaks - Anglers Reef 119 - Islamorada, FL
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.
Island Escape In Islamorada | Breakfast, Pool & Pet-friendly Stay! - Islamorada, FL
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.
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