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Islamorada, FL villas
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528 Villa rentals in Islamorada, FL

Seashore Holiday Homes in Islamorada, FL, United States

Open your glass doors and step directly from your living room onto the soft sand at houses on the seashore in Islamorada, FL, United States.

288 M² House ∙ 4 Bedrooms ∙ 10 Guests - Islamorada, FL
10 1 review

288 M² House ∙ 4 Bedrooms ∙ 10 Guests

house, Islamorada, Village of Islands
This substantial detached house in Islamorada, Village of Islands, boasts a unique waterfront position with a private beach and dock, offering direct ocean access for swimming and fishing.
With 288 square meters of living space, this property accommodates up to 10 guests across four bedrooms and four bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace, garden, and a boat ramp.

Holiday Homes and Beach Houses with a Pool in Islamorada, FL, United States

Swim laps in total seclusion surrounded by swaying palm trees at beach houses with a private pool in Islamorada, FL, United States.

Sunshine Paradise Key Largo Ocean Pointe 4402 - Islamorada, FL
10 2 reviews

Sunshine Paradise Key Largo Ocean Pointe 4402

house, Tavernier
Sunshine Paradise Key Largo Ocean Pointe 4402, a two-bedroom house in Tavernier, Key Largo, offers oceanfront proximity, a 15-minute walk from Harry Harris Park Beach, and is 4.5km from Pigeon Key and 13km from Windley Key.
This 77-square-metre property boasts two bathrooms, sleeps seven guests, and includes a private entrance, swimming pool, Jacuzzi, free Wi-Fi, and a fully equipped kitchen with dishwasher; in-unit laundry facilities are also provided.
Bungalow #4 - 2 Bed/1 Bath & Pool In Islamorada - Islamorada, FL
9.7 95 reviews

Bungalow #4 - 2 Bed/1 Bath & Pool In Islamorada

apartment, Islamorada, Village of Islands
This charming bungalow is situated just a short distance from the lively downtown area of Islamorada, offering easy access to the renowned fishing piers and the scenic Overseas Highway. The property has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The cottage comfortably accommodates up to four guests across two bedrooms and one bathroom, spanning 88 square metres. Guests can enjoy a private backyard and porch, a community heated pool, a fully equipped kitchen with modern appliances, a washer and dryer, complimentary bicycles, and a security camera for added peace of mind.
Serenity By The Sea!!  Anglers Reef With Boat Slip Available!! - Islamorada, FL
10 125 reviews

Serenity By The Sea!! Anglers Reef With Boat Slip Available!!

house, Islamorada, Village of Islands
This two-bedroom villa is located in the gated community of Angler's Reef in Islamorada, just a short drive from the best restaurants and attractions in the Keys. The property has received excellent user ratings, reflecting its desirable location and amenities.
The villa offers 128 square metres of living space, accommodating up to six guests comfortably. Guests can enjoy a private boat slip, a heated pool, two private beaches, and a range of water activities, including kayaking, paddleboarding, fishing, and boating.
Islamorada | Maison Residences - Islamorada, FL
9.8 13 reviews

Islamorada | Maison Residences

house, Islamorada, Village of Islands
This luxurious four-bedroom Maison Residences apartment in Islamorada, Florida Keys, boasts direct access to a private beach and is conveniently located near various local attractions.
The 290 square metre property features an open-plan layout, accommodating up to ten guests, and includes a private pool, jacuzzi, and access to a 107-metre dock, perfect for water activities.

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Best Islamorada, FL villas and holiday homes with a kitchen

House ∙ 2 Bedrooms ∙ 8 Guests - Islamorada, FL
No reviews

House ∙ 2 Bedrooms ∙ 8 Guests

house, Islamorada, Village of Islands
This Leatherback Cottage is located in Turtle Cove, an oceanfront enclave within Islamorada, Village of Islands, offering direct access to the open ocean.
This two-bedroom, three-bathroom holiday home accommodates eight guests and features a separate lower-level unit with a kitchenette, plus shared access to a swimming pool, boat basin, and various water sports equipment.
683 M² House ∙ 9 Bedrooms ∙ 18 Guests - Islamorada, FL
No reviews

683 M² House ∙ 9 Bedrooms ∙ 18 Guests

house, Islamorada, Village of Islands
This exclusive estate is located on Florida Bay in Islamorada, Village of Islands, offering direct access to a 100-foot deep-water dock and situated approximately three hours by car south of Key West, with downtown shops, dining, and attractions nearby.
This luxurious 9-bedroom residence and detached 2-bedroom apartment provide over 7,000 square feet of living space for up to 18 guests, featuring a chef's kitchen, infinity pool, outdoor kitchen, and an integrated Sonos sound system for indoor and outdoor entertainment.
Isla Lychee: Boutique Resort, Free Boat Dockage Sep-oct Only! - Islamorada, FL
9.8 8 reviews

Isla Lychee: Boutique Resort, Free Boat Dockage Sep-oct Only!

house, Islamorada, Village of Islands
Isla Lychee: Little Basin Villas, a waterfront boutique resort in Matecumbe, Islamorada, is within walking distance of the Islamorada Brewery & Distillery and Keys History & Discovery Centre, and less than 2.4km from the History of Diving Museum.
This 156 square metre, three-bedroom villa sleeps six, offering four bathrooms, a fully equipped kitchen, free Wi-Fi, a private balcony, and access to on-site barbecue grills.
Sandglass 4 - Islamorada, FL
No reviews

Sandglass 4

house, Islamorada, Village of Islands
Sandglass 4, a five-bedroom house in Islamorada, offers direct beach access to Sea Oats Beach and is 2.3km from Anne's Beach, 11km from Upper Matecumbe Key, and 16km from Windley Key.
This 208-square-metre property sleeps 23 guests and boasts a fully equipped kitchen, spa, fitness centre, free Wi-Fi, and ample parking, making it ideal for large families or groups seeking a luxurious Islamorada getaway.

Best Islamorada, FL villas and holiday homes with air conditioning

Private Beach & Dock  / Heated Pool / Dolphin Key - Islamorada, FL
No reviews

Private Beach & Dock / Heated Pool / Dolphin Key

house, Islamorada, Village of Islands
This oceanfront villa in Islamorada, Village of Islands, offers direct access to a secluded private beach, perfect for a tranquil coastal escape.
This four-bedroom property accommodates eight guests and features a heated swimming pool, a private dock, an elevator, and gigabit Wi-Fi for a comfortable and entertaining stay.
House ∙ 8 Bedrooms ∙ 16 Guests - Islamorada, FL
No reviews

House ∙ 8 Bedrooms ∙ 16 Guests

house, Islamorada, Village of Islands
This oceanfront residence in Islamorada, Village of Islands, is located near the Arts and Culture District and is approximately a 145-kilometre drive from Miami, with seaplane access available on the bay.
This spacious villa offers direct oceanfront access with private beach steps, an 86-foot lagoon-style pool, a heated jacuzzi, two full kitchens, outdoor kitchens, and accommodation for 16 guests, alongside an optional 32-foot boat slip.
Forever Views - Islamorada, FL
10 10 reviews

Forever Views

house, Islamorada, Village of Islands
This three-bedroom property is located in the Bay Harbour gated community at Mile Marker 77.5, just a short walk from a beach and less than 1.6 kilometres from Anne's Beach. This accommodation has received excellent ratings for its cleanliness, location and user experience.
The property offers a spacious layout, comfortably accommodating up to six guests. It has a fully equipped kitchen, a private dock, a screened terrace, a swimming pool, a spa, a fitness centre and a range of other amenities that make for a relaxing and enjoyable stay.
2402 Ocean Pointe - Islamorada, FL
8.3 3 reviews

2402 Ocean Pointe

house, Tavernier
Ocean Pointe apartment in Tavernier, Florida Keys, enjoys a prime location, just 19 kilometres from Upper Matecumbe Key and 15 kilometres from Windley Key Fossil Reef.
This two-bedroom, two-bathroom flat, boasting 79 square metres of floor space, sleeps up to 11 guests and includes a fully equipped kitchen, swimming pool, jacuzzi, and free Wi-Fi; Harry Harris Park Beach is a short 13-minute walk away.

Holiday Homes with a Hot Tub in Islamorada, FL, United States

Watch the ocean stars from the bubbling warmth of a private shoreline hot tub at beach houses in Islamorada, FL, United States.

Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp - Islamorada, FL
10 178 reviews

Tikibar With Tv &Stereo, Privatespa, Heated Pool, Hammock,sups, Kayaks,bikes,fp

apartment, Islamorada, Village of Islands
Brand New Oceanside Paradise Waterfront With Pool And Hot Tub - Islamorada, FL
10 1 review

Brand New Oceanside Paradise Waterfront With Pool And Hot Tub

house, Key Largo
Ocean View Gem Ocean Pointe 3406 - Islamorada, FL
8.9 16 reviews

Ocean View Gem Ocean Pointe 3406

house, Tavernier
Private Beach Heated Pool Volleyball Court Orchid Beach Key - Islamorada, FL
No reviews

Private Beach Heated Pool Volleyball Court Orchid Beach Key

house, Islamorada, Village of Islands

View Exclusive Luxury Houses in Islamorada, FL, United States

Bask in private tropical exclusivity with premier shoreline architecture and absolute privacy at luxury houses by the sea in Islamorada, FL, United States.

62 M² Villa ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
10 14 reviews

62 M² Villa ∙ 2 Bedrooms ∙ 4 Guests

house, Islamorada, Village of Islands

Find the Best Family Houses in Islamorada, FL, United States

Give the family an unforgettable seaside holiday with a massive kitchen and direct sand access at family beach houses in Islamorada, FL, United States.

Private Beach  / Heated Pool / Private Dock / Dolphin Key - Islamorada, FL
No reviews

Private Beach / Heated Pool / Private Dock / Dolphin Key

house, Islamorada, Village of Islands
House ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
No reviews

House ∙ 2 Bedrooms ∙ 4 Guests

house, Islamorada, Village of Islands
164 M² Ferienhaus ∙ 3 Schlafzimmer ∙ 6 Gäste - Islamorada, FL
10 11 reviews

164 M² Ferienhaus ∙ 3 Schlafzimmer ∙ 6 Gäste

house, Islamorada, Village of Islands
345 M² House ∙ 3 Bedrooms ∙ 10 Guests - Islamorada, FL
No reviews

345 M² House ∙ 3 Bedrooms ∙ 10 Guests

house, Islamorada, Village of Islands

Best Islamorada, FL villas and holiday homes with parking

Isla Mirabelle: Boutique Resort, Free Boat Dockage Sep-oct Only! - Islamorada, FL
10 8 reviews

Isla Mirabelle: Boutique Resort, Free Boat Dockage Sep-oct Only!

house, Islamorada, Village of Islands
New Tropical Escape Sea Gulls 407 - Islamorada, FL
9.5 4 reviews

New Tropical Escape Sea Gulls 407

house, Islamorada, Village of Islands
Oceanfront Islamorada Townhome With Pool & Dock - Islamorada, FL
10 8 reviews

Oceanfront Islamorada Townhome With Pool & Dock

house, Islamorada, Village of Islands
139 M² House ∙ 3 Bedrooms ∙ 8 Guests - Islamorada, FL
No reviews

139 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Islamorada, Village of Islands

Top-Rated Holiday Homes with Free Breakfast in Islamorada, FL, United States

Find beach houses with free breakfast in Islamorada, FL, United States and start each morning with ease.

Isla Key Acaí: Waterfront Boutique Resort, Free Boat Dockage Sep-oct Only! - Islamorada, FL
9.8 9 reviews

Isla Key Acaí: Waterfront Boutique Resort, Free Boat Dockage Sep-oct Only!

house, Islamorada, Village of Islands
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