Islamorada, FL Short term rentals

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Islamorada, FL short term rentals
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Best Short term and Weekly rentals in Islamorada, FL

Search Family Short-Term Rentals in Islamorada, FL

Family beach days in Islamorada, FL are easier when your rental offers enough square footage for everyone to relax.

208 M² Condo ∙ 5 Bedrooms ∙ 12 Guests - Islamorada, FL
10 3 reviews
Islamorada, FL
06/20 – 06/27
$794/nighttotal: $5558 (7 )

208 M² Condo ∙ 5 Bedrooms ∙ 12 Guests

5 6
apartment , Islamorada, Village of Islands
Sandglass 4, a bayside townhouse in Islamorada's Lower Matecumbe district at mile marker 74.9, offers direct Florida Bay access with a private boat ramp and dockage for boats up to 30 feet.
This 2240-square-foot Islamorada vacation rental boasts five bedrooms, three bathrooms, sleeps twelve, and includes a large kitchen, screened balcony with 180-degree ocean views, a spa, fitness center, and contactless check-in/out.
Aquamarine Oceanview+special Rates+\ndock+pool+gym+spa+1535 Star Reviews!!! - Islamorada, FL
10 158 reviews
Islamorada, FL
06/20 – 06/27
$430/nighttotal: $3010 (7 )

Aquamarine Oceanview+special Rates+\ndock+pool+gym+spa+1535 Star Reviews!!!

2 2
apartment , Islamorada, Village of Islands
This waterfront apartment in Matecumbe, Islamorada, offers a unique 5-star experience with its private dock, heated pool, hot tub, and lighted tennis courts. It is highly rated by previous guests for its cleanliness, comfort, and amenities.
The apartment features 2 bedrooms, 3 bathrooms, and a floor area of 1700 square feet, comfortably accommodating up to 6 guests. It boasts a fully equipped kitchen, a spacious living area, and a private terrace overlooking the water. Guests can enjoy complimentary amenities such as bikes, pool toys, and a freezer for bait/catch, as well as access to a concierge service for assistance with activities and arrangements.
Oceanfront Views At Ocean Pointe + Pool + Beach & Marina Access, Updated 2br - Islamorada, FL
9.3 124 reviews
Islamorada, FL
07/18 – 07/22
$470/nighttotal: $1880 (4 )

Oceanfront Views At Ocean Pointe + Pool + Beach & Marina Access, Updated 2br

2 4
apartment , Tavernier
This Tavernier vacation rental is conveniently located within walking distance of Baker's Cay Resort Beach and Harry Harris Park, offering easy access to Tavernier's most popular attractions. The property has received excellent ratings for location, cleanliness, and user experience.
This 2-bedroom, 2-bathroom apartment comfortably accommodates up to 6 guests in its 840 square feet of space. Guests can enjoy amenities such as a private pool, a spa tub, a fully equipped kitchen, and a balcony.
Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar - Islamorada, FL
9.1 74 reviews
Islamorada, FL
07/09 – 07/12
$387/nighttotal: $1161 (3 )

Tavernier Oceanfront Resort Condo-pool, Dockage, Kayaks, Onsite Restaurant & Bar

2 5
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.

Best Islamorada, FL lodging with a balcony

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 Degree Ocean Views - Islamorada, FL
10 116 reviews
Islamorada, FL
07/03 – 07/10
$2192/nighttotal: $15344 (7 )

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 Degree Ocean Views

5 8
apartment , Islamorada, Village of Islands
This oceanfront vacation home is located in the Matecumbe district of Islamorada, just a half mile from Robbie's of Islamorada and a short paddle from Alligator Reef Lighthouse. The property is rated excellent by previous guests and offers exceptional privacy and natural beauty on a private beach with a natural seawall.
This 5-bedroom, 5-bathroom home comfortably accommodates up to 10 guests and offers 2,450 square feet of living space. Enjoy the private oceanfront pool, paddleboards, kayaks, fishing dock, and a well-equipped kitchen with a fridge, microwave, and dishwasher.
2402 Ocean Pointe - 2 Bedroom Condo Upgraded With Clean Lines And Coastal Colors - Islamorada, FL
9.2 30 reviews
Islamorada, FL
07/25 – 08/01
$405/nighttotal: $2835 (7 )

2402 Ocean Pointe - 2 Bedroom Condo Upgraded With Clean Lines And Coastal Colors

2 5
apartment , Tavernier
This Tavernier condo, near Harry Harris Park, Mariners Hospital, and Pigeon Key, offers easy access to recreation, healthcare, and historical sites.
The 850-square-foot unit features two bedrooms, two bathrooms, a sofa bed accommodating up to six guests, and amenities including a pool, jacuzzi, and free Wi-Fi.
Luxury 3 Bedroom Condo Overlooking Harbor With Ocean View, Boat Slip, Amenities - Islamorada, FL
10 99 reviews
Islamorada, FL
10/17 – 10/26
$554/nighttotal: $4986 (9 )

Luxury 3 Bedroom Condo Overlooking Harbor With Ocean View, Boat Slip, Amenities

3 6
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.
118 M² Condo ∙ 2 Bedrooms ∙ 4 Guests - Islamorada, FL
Islamorada, FL
09/08 – 10/06
$200/nighttotal: $5600 (28 )

118 M² Condo ∙ 2 Bedrooms ∙ 4 Guests

2 4
apartment , Islamorada, Village of Islands
This oceanfront condo in Islamorada, the Sport Fishing Capital of the World, offers direct beach and water access.
This 1270 sq ft, 2-bedroom, 2-bathroom condo accommodates up to 4 guests and features a gourmet kitchen, private dock with boat slips and tiki hut, community pool, spa, fitness center, and BBQ area.

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Best Islamorada, FL lodging with a kitchen

By The Sea ~ Islamorada Home With Ocean Views! - Islamorada, FL
9.4 10 reviews
Islamorada, FL
07/25 – 08/01
$491/nighttotal: $3437 (7 )

By The Sea ~ Islamorada Home With Ocean Views!

2 5
apartment , Islamorada, Village of Islands
This vacation home is located in the tranquil Matecumbe district of Islamorada, Village of Islands, within walking distance of Sunset Drive Beach and San Pedro Underwater Archaeological Preserve State Park. The house has received excellent user ratings.
The house has 2 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. It features a fully equipped kitchen, a private balcony, a garden, and air conditioning. Guests can enjoy activities such as swimming, sunbathing, water sports, and diving.
Ocean View 2br Condo  Pool, Beach, Near The Fun - Islamorada, FL
Islamorada, FL
07/03 – 07/05
$571/nighttotal: $1142 (2 )

Ocean View 2br Condo Pool, Beach, Near The Fun

2 5
apartment , Tavernier
This Tavernier oceanfront condo, near Key Largo and Islamorada, provides private beach access and proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park.
This 850-square-foot rental boasts two bedrooms, two bathrooms, sleeps six, and includes a full kitchen, swimming pool, and parking; resort amenities such as a Jr. Olympic pool, hot tub, and tennis courts are also available.
4 Bedroom House In Angler's Reef, Includes 31' Boat Slip. Islamorada, Fl - Islamorada, FL
10 121 reviews
Islamorada, FL
10/17 – 10/26
$614/nighttotal: $5526 (9 )

4 Bedroom House In Angler's Reef, Includes 31' Boat Slip. Islamorada, Fl

4 6
apartment , Islamorada, Village of Islands
This boat is located in Angler's Reef, a gated community in Islamorada, just a short distance from the Florida Keys Brewing Co. and Florida Keys Dive Center, making it a convenient base for exploring the area. It has received excellent user ratings, so you can be sure of a comfortable stay. This spacious vacation rental offers 1980 square feet of living space and can accommodate up to 8 guests, making it ideal for families or groups of friends. The boat features a fully equipped kitchen, a private pool, a hot tub, and a spacious terrace, providing everything you need for a relaxing and enjoyable vacation.
Islamorada Beach | Beachfront, Fire Pit & Pool - Islamorada, FL
9.8 8 reviews
Islamorada, FL
07/03 – 07/10
$2916/nighttotal: $20412 (7 )

Islamorada Beach | Beachfront, Fire Pit & Pool

1 8
apartment , Islamorada, Village of Islands
Wander Islamorada Beach, a beachfront property in Islamorada, Florida, offers direct access to a secluded cove and is conveniently located near other Village of Islands attractions.
This three-story house boasts six bedrooms, five bathrooms, and three living rooms, comfortably accommodating up to twelve guests, and includes amenities such as a private pool, two outdoor terraces, two paddle boards, two kayaks, a fully equipped kitchen, and high-speed Wi-Fi.

Best Islamorada, FL lodging with laundry available

Ocean View Gem Ocean Pointe 3406 2ba/2br King/queen - Islamorada, FL
9.8 7 reviews
Islamorada, FL
07/09 – 07/12
$405/nighttotal: $1215 (3 )

Ocean View Gem Ocean Pointe 3406 2ba/2br King/queen

2 5
apartment , Tavernier
This oceanfront Tavernier condo, located 0.6 miles from Harry Harris Park and within 3 miles of Mariners Hospital and the Florida Keys Dive Center, offers stunning ocean views and easy beach access.
The 830-square-foot rental boasts three bedrooms, two bathrooms, sleeps five, and includes a fully equipped kitchen, private balcony, swimming pool, jacuzzi, and on-site barbecue grills.
Life On A Rock Luxury Home In Downtown Islamorada - Islamorada, FL
10 4 reviews
Islamorada, FL
09/08 – 10/06
$256/nighttotal: $7168 (28 )

Life On A Rock Luxury Home In Downtown Islamorada

1 4
apartment , Islamorada, Village of Islands
This Islamorada condo offers immediate access to dining, entertainment, and shopping venues, with a neighborhood beach located approximately 1,320 feet away.
This 2-bedroom, 2-bathroom unit accommodates up to 4 guests and features Tommy Bahama furnishings, Tempur-Pedic mattresses, air conditioning, internet, kitchen, and parking.
Oceanfront Keys Escape | Private Beach & Pool | 3 Acres - Islamorada, FL
10 52 reviews
Islamorada, FL
07/03 – 07/10
$1627/nighttotal: $11389 (7 )

Oceanfront Keys Escape | Private Beach & Pool | 3 Acres

1 8
apartment , Islamorada, Village of Islands
This beautiful vacation rental is located in Islamorada, just a short drive from the popular Islamorada Fish Company and the Theater of the Sea. The accommodation has received excellent ratings for its location, cleanliness, and overall experience.
This 3-bedroom home can accommodate up to 8 guests and features a spacious 2,000 square foot layout. Guests will enjoy a private beach, an oceanfront pool, a fitness center, a spa, and a variety of other amenities.
Islamorada Bungalow #5 - Islamorada, FL
9.7 28 reviews
Islamorada, FL
08/09 – 08/14
$360/nighttotal: $1800 (5 )

Islamorada Bungalow #5

1 2
apartment , Islamorada, Village of Islands
This Islamorada, Florida bungalow offers a convenient, centrally located base for exploring the Village of Islands, providing easy access to nearby beaches and renowned fishing spots.
The 2-bedroom, 1-bathroom house sleeps 4, features a fully equipped kitchen, in-unit laundry, a private patio, community pool access, and on-site bicycles for guest use.
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