Vacation rentals in Islamorada, FL

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Islamorada, FL vacation rentals
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Best Vacation rentals and Airbnb offers in Islamorada, FL

Best Islamorada, FL vacation rentals with a balcony

Bay Harbour Islamorada Oceanfront Views 3/2.5 Updated Condo Dock - Islamorada, FL
10 24 reviews

Bay Harbour Islamorada Oceanfront Views 3/2.5 Updated Condo Dock

apartment, Islamorada, Village of Islands
This 3-bedroom, 2-bathroom Islamorada condo is located in the gated Bay Harbour community at MM 77.5 bayside, within a mile of Anne's Beach and near San Pedro Underwater Archaeological Preserve State Park.
This waterfront condominium offers a private screened terrace with sunrise views, a gourmet kitchen, expansive ocean-view glass doors, and a 31-foot dock with a boat lift, accommodating up to 6 guests with amenities including air conditioning, a swimming pool, and Wi-Fi.
Ocean Front Paradise, 6th Story Balcony Ocean View - Islamorada, FL
9.4 6 reviews

Ocean Front Paradise, 6th Story Balcony Ocean View

apartment, Islamorada, Village of Islands
This Tavernier condo, located three miles from the Florida Keys Dive Center, Old Road Gallery, and Mariners Hospital, offers direct beach access and proximity to Islamorada's attractions.
This 1180-square-foot, two-bedroom, two-bathroom unit sleeps four and features a fully equipped kitchen, swimming pool, spa, fitness center, tennis court, and free Wi-Fi.
Luxury Condo With Boat Slip Overlooking The Bay - Islamorada, FL
10 100 reviews

Luxury Condo With Boat Slip Overlooking The Bay

apartment, Islamorada, Village of Islands
This family-friendly condo building is located on the waterfront in Islamorada, just a mile from Sunset Drive Beach and Anne's Beach, and a short drive from San Pedro Underwater Archaeological Preserve State Park. The apartment has received excellent ratings for user experience, location, and cleanliness.
This 3-bedroom, 2020 square foot apartment comfortably accommodates up to 6 guests. Enjoy amenities such as a private pool, a fenced yard, a fitness center, a spa tub, and barbecue grills, as well as a full kitchen and internet access.
Keys Resort Condo W Marina, Pool, Bar & Beach View - Islamorada, FL
9.0 78 reviews

Keys Resort Condo W Marina, Pool, Bar & Beach View

apartment, Tavernier
This apartment in Tavernier is a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park. It is highly rated for its location, cleanliness, and user experience.
The apartment has two bedrooms, two bathrooms, a sofa bed, and a floor area of 830 square feet. It can accommodate up to six guests. Amenities include a private pool, concierge services, barbecue grills, a washing machine, and a smoke-free environment.

Our Favorite Family-Friendly Vacation Rentals in Islamorada, FL

Find the perfect family vacation rental or Airbnb in Islamorada, FL with plenty of room to spread out near local beaches.

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included. - Islamorada, FL
10 125 reviews

Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.

apartment, Islamorada, Village of Islands
Angler's Reef, a luxury waterfront villa located at mile marker 85 in Islamorada, offers a private boat slip (up to 31 feet), community kayaks, and proximity to Indian Key Historic State Park and San Pedro Underwater Archaeological Preserve State Park.
This 2200-square-foot, four-bedroom, three-bathroom vacation home sleeps eight guests and boasts a fully remodeled chef's kitchen, expansive wrap-around balconies, a swimming pool, spa, and family-friendly amenities like a highchair, booster seat, and pack 'n play.
Relax In Your One Bedroom Oceanfront Suite In Tavernier Fl. Florida Keys. - Islamorada, FL
9.6 90 reviews

Relax In Your One Bedroom Oceanfront Suite In Tavernier Fl. Florida Keys.

apartment, Tavernier
This Tavernier condo is conveniently located near Harry Harris Park (0.6 miles), Mariners Hospital (under 3 miles), and within a 6-mile radius of Old Road Gallery and Bluefin Rock Harbor Marina.
This one-bedroom, one-bathroom apartment sleeps four, boasts a fully equipped kitchen, in-unit laundry, private balcony, free Wi-Fi, and access to a community pool, hot tub, and tennis court.
Light, Bright & Nautical Condo At Ocean Pointe - Islamorada, FL
9.9 179 reviews

Light, Bright & Nautical Condo At Ocean Pointe

apartment, Tavernier
This waterfront condo in Tavernier is located just a 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, offering easy access to the beautiful Florida Keys. This rental has earned excellent ratings for its cleanliness, location, and overall user experience.
The 950-square-foot apartment comfortably sleeps four guests in its two bedrooms and two bathrooms. Enjoy swimming, relaxing in the Jacuzzi, grilling outdoors, and taking advantage of the tennis court, all while taking in the stunning waterfront views from your private balcony.
Oceanside Family Condo With Pool And Beach Access - Islamorada, FL
No reviews

Oceanside Family Condo With Pool And Beach Access

house, Tavernier
This oceanside condo in Tavernier is located a short walk from Harry Harris Park Beach and 3 miles from Pigeon Key, with Miami International Airport 65 miles away.
This 930 sq ft, two-bedroom, two-bathroom unit accommodates up to 11 guests and features a sea-view balcony, an outdoor swimming pool, an on-site spa, and a hot tub.

Frequently Asked Questions about vacation rentals in Islamorada, FL

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Best Islamorada, FL vacation rentals with parking

Starfish Seas Key Largo Ocean Pointe 1302 - Islamorada, FL
9.8 26 reviews

Starfish Seas Key Largo Ocean Pointe 1302

house, Tavernier
Starfish Seas Key Largo Ocean Pointe 1302, located in Key Largo, offers ocean views and is a short walk from Harry Harris Park Beach, with easy access to Pigeon Key and other attractions like John Pennekamp State Park.
This 830-square-foot Key Largo vacation home features two bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, swimming pool, Jacuzzi, and free Wi-Fi.
Flamingo Flats Ocean Pointe 5306 - Islamorada, FL
9.8 6 reviews

Flamingo Flats Ocean Pointe 5306

house, Tavernier
Flamingo Flats Ocean Pointe 5306, a Key Largo vacation home, is a short drive from Harry Harris Park Beach and 2.8 miles from Pigeon Key.
This 830-square-foot rental boasts two bedrooms, two bathrooms, accommodates six guests, and includes a private patio with ocean views, a pool, a fully equipped kitchen, Wi-Fi, cable TV, and a washer.
Anglers Reef 103 - 2 Br - Beach Access Kayaks - Islamorada, FL
9.7 7 reviews

Anglers Reef 103 - 2 Br - Beach Access Kayaks

house, Islamorada, Village of Islands
Angler's Reef Resort is located in Islamorada, a short distance from Anne's Beach and within a 10-mile radius of Upper Matecumbe Key and Windley Key. The resort has received excellent ratings for location, cleanliness, and overall user experience.
The resort offers a variety of accommodations, including rooms with private bathrooms and some with kitchens. Amenities include a private beach, a tranquil garden, an outdoor pool, BBQ facilities, free parking, and WiFi. Guests can also enjoy activities like cycling and exploring the surrounding area.
Discover Florida Keys! Seaside Villa W/ Patio! Marina, Pool, Parking, Breakfast - Islamorada, FL
8.4 5 reviews

Discover Florida Keys! Seaside Villa W/ Patio! Marina, Pool, Parking, Breakfast

apartment, Islamorada, Village of Islands
This vacation home is located in Islamorada, directly on the beach in the village's center, offering easy access to Florida Keys Brewing Co. and Bud n' Mary's Dive Center. The property features one bedroom, one bathroom, and a floor area of 290 square feet, comfortably accommodating up to four guests.
The accommodation offers a private beach, a heated pool with ocean views, and a private boat ramp for an additional fee. Guests can enjoy daily continental breakfast, outdoor BBQ facilities, and on-site amenities like stand-up paddle boards, kayaks, and bicycles.

Search Vacation Rentals with Swimming Pool in Islamorada, FL

Choose a vacation rental with a pool in Islamorada, FL to perfectly complement your day of adventures.

New Oceanside Paradise With Pool And Waterfront Views! - Islamorada, FL
10 2 reviews

New Oceanside Paradise With Pool And Waterfront Views!

apartment, Key Largo
This beachfront Key Largo vacation home, located in a gated community near local eateries and a marina with jet ski rentals, offers stunning Atlantic Ocean views.
This three-story, 2,690-square-foot residence boasts three bedrooms, three bathrooms, a rooftop deck, private hot tub, and community access to a pool, kayaks, and paddleboards; it comfortably sleeps nine guests.
Chesapeake Beach Resort - Islamorada, FL
9.0 2606 reviews

Chesapeake Beach Resort

resort, Islamorada, Village of Islands
Chesapeake Beach Resort is located in Islamorada, Florida, just two miles from Windley Key Fossil Reef Geological State Park, offering easy access to both the beach and nearby attractions. The resort consistently receives very good ratings for its location, cleanliness, and overall experience.
The resort offers a variety of rooms and suites, all featuring comfortable furnishings and modern amenities. Guests can enjoy a refreshing swim in the outdoor pool, relax in the hot tub, or take advantage of the on-site restaurant, bar, and room service.
3 Bedroom Islamorada Condo W/ 30' Boat Slip & Ocean Views! - Islamorada, FL
10 2 reviews

3 Bedroom Islamorada Condo W/ 30' Boat Slip & Ocean Views!

apartment, Islamorada, Village of Islands
This Islamorada waterfront condo, located in Matecumbe, offers direct dock access, proximity to Anne's Beach (1.5 miles), and is a short drive from Robbie's Marina (5 minutes) and downtown Islamorada (10 minutes).
This 2,020-square-foot vacation rental boasts three bedrooms, three bathrooms, sleeps six, and includes a private balcony with ocean views, a fully equipped kitchen with a coffee bar and air fryer, resort-style amenities (pool, hot tub, fitness center, tennis/pickleball courts), and a private dock for boat rentals and fishing.
Key Largo Coastal Condo-ocean View ~ Pool ~ Beach - Islamorada, FL
9.8 219 reviews

Key Largo Coastal Condo-ocean View ~ Pool ~ Beach

apartment, Tavernier
This waterfront condo is located in Tavernier, a short 15-minute walk from Baker's Cay Resort Beach and Harry Harris Park, and within 3 miles of Mariners Hospital and Florida Keys Dive Center. This rental has excellent user, location, and cleanliness ratings.
The condo has one bedroom, one bathroom, and can accommodate up to three guests in its 580 square feet. Enjoy the pool, spa, tennis court, and other amenities, including a fully equipped kitchen, a fireplace, and a washer and dryer.

Search Coastal Vacation Rentals near Islamorada, FL

These seaside vacation rentals in Islamorada, FL provide an excellent base for exploring the coast. Browse top local properties and plan your beach-town trip.

Beach View Unit In Islamorada! Pets Allowed, Parking, Pool & Free Breakfast! - Islamorada, FL
8.6 29 reviews

Beach View Unit In Islamorada! Pets Allowed, Parking, Pool & Free Breakfast!

apartment, Islamorada, Village of Islands
New Pool ** Waterfront Paradise With Amazing Sunsets On Beach** - Islamorada, FL
10 31 reviews

New Pool ** Waterfront Paradise With Amazing Sunsets On Beach**

apartment, Islamorada, Village of Islands
Keys Getaway Den Suite | Room For The Crew - Islamorada, FL
No reviews

Keys Getaway Den Suite | Room For The Crew

apartment, Islamorada, Village of Islands
Exceptional Vaca In Angler's Reef Islamorada - Islamorada, FL
10 68 reviews

Exceptional Vaca In Angler's Reef Islamorada

house, Islamorada, Village of Islands

Browse Luxury Vacation Rentals in Islamorada, FL

Premium waterfront rentals in Islamorada, FL combine upscale design with refined service for a truly superior getaway.

Oceanfront Studio In Islamorada, Behind Main House - Islamorada, FL
10 1 review

Oceanfront Studio In Islamorada, Behind Main House

apartment, Islamorada, Village of Islands

Choose the Right Vacation Rentals with a Steam Room in Islamorada, FL

Relax with an on-site sauna at these vacation rentals in Islamorada, FL, perfect for a steam session after a day by the water.

Luxury 3br Coastal Escape In Islamorada - Islamorada, FL
No reviews

Luxury 3br Coastal Escape In Islamorada

apartment, Islamorada, Village of Islands
Cheeca Lodge & Spa - Islamorada, FL
8.8 219 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Oceanfront 4br Retreat W/ Private 31' Boat Slip, Pool & Beach, Gourmet Kitchen - Islamorada, FL
9.8 47 reviews

Oceanfront 4br Retreat W/ Private 31' Boat Slip, Pool & Beach, Gourmet Kitchen

apartment, Islamorada, Village of Islands
Islamorada Oceanfront Luxury Living - Islamorada, FL
No reviews

Islamorada Oceanfront Luxury Living

apartment, Islamorada, Village of Islands
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