Search All Cottages in Longboat Key, FL

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Longboat Key, FL cottages
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38 Cottages at the best price in Longboat Key, FL

Guest-Favourite Family-Friendly Cottages in Longboat Key, FL

Choosing a family-friendly cottage in Longboat Key, FL ensures a perfectly tailored, stress-free holiday for all ages.

Charming Ground Level Resort Style 3 Unit Condo  - Unit C - Longboat Key, FL
9.8 36 reviews
Longboat Key, FL
22/08 – 05/09
£246/nighttotal: £3444 (14 )

Charming Ground Level Resort Style 3 Unit Condo - Unit C

2 3
cottage , Holmes Beach
This charming ground floor apartment, part of a three-unit complex, is conveniently located in Ilexhurst, Holmes Beach, just a short walk from Anna Maria Sound and Bradenton Beach. It has consistently received excellent reviews from previous guests. This two-bedroom apartment, spanning 84 square metres, comfortably accommodates up to six guests. Amenities include a private pool, a garden with barbecue facilities, free Wi-Fi, and a fully equipped kitchen.
Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included - Longboat Key, FL
10 12 reviews
Longboat Key, FL
22/08 – 05/09
£442/nighttotal: £6188 (14 )

Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included

2 3
cottage , Holmes Beach
This Holmes Beach seaside cottage, near Bradenton Beach, is a 10-minute walk from Island Gallery West and under 2km from both Holmes Beach and Manatee Public Beaches.
This 96 square metre holiday home sleeps six, boasting two bedrooms, one bathroom, a private pool, hot tub, barbecue, and fully equipped kitchen including a dishwasher; free Wi-Fi is also provided.
Quiet Nights Of Quiet Stars On Anna Maria Island - Longboat Key, FL
10 143 reviews
Longboat Key, FL
26/12 – 31/12
£144/nighttotal: £720 (5 )

Quiet Nights Of Quiet Stars On Anna Maria Island

2 2
cottage , Holmes Beach
This Holmes Beach cottage boasts beachfront access, a 10-minute walk from Bradenton Beach and Island Gallery West, and under 2km from Holmes Beach and Manatee Public Beach.
This 65 square metre holiday home sleeps four in two bedrooms, one bathroom, and includes a fully equipped kitchen, free Wi-Fi, a terrace, garden, tennis court, parking, and on-site barbecue facilities.
Retro Style Home With Large Pool Close To Downtown Holmes Beach And Walk To Beach! - Longboat Key, FL
10 6 reviews
Longboat Key, FL
22/08 – 05/09
£298/nighttotal: £4172 (14 )

Retro Style Home With Large Pool Close To Downtown Holmes Beach And Walk To Beach!

2 3
cottage , Holmes Beach
This Holmes Beach holiday home is ideally situated less than 0.8km from Island Gallery West and Bradenton Beach, with AMI Paddleboard Adventures and Holmes Beach's shores within a 2.4km radius.
The two-bedroom, three-bathroom property sleeps four, boasting a private pool, barbecue, fully equipped kitchen including a dishwasher, and amenities such as a DVD player and balcony; pets are welcome.

Best Longboat Key, FL cottages with a garden

Blue Agave Villa By Beach Boutique Rentals - Longboat Key, FL
9.8 105 reviews
Longboat Key, FL
22/08 – 05/09
£309/nighttotal: £4326 (14 )

Blue Agave Villa By Beach Boutique Rentals

2 3
cottage , Holmes Beach
Frangipani Villa is a ground-floor holiday home in Holmes Beach, just a short walk from the beach path and within easy reach of shops and restaurants. The villa has received excellent ratings for location, cleanliness, and overall user experience.
The cottage features a private outdoor shower, a spacious porch with Adirondack chairs, and a fully equipped kitchen. Guests can enjoy a botanical courtyard with a fountain, relax on the porch, or take advantage of the beach supplies provided.
Romantic, Cute Cottage On Anna Maria Island. Close To Everything. Pet Friendly! - Longboat Key, FL
10 23 reviews
Longboat Key, FL
22/08 – 05/09
£360/nighttotal: £5040 (14 )

Romantic, Cute Cottage On Anna Maria Island. Close To Everything. Pet Friendly!

2 3
cottage , Bradenton Beach
This Bradenton Beach holiday home is ideally located just steps from Fish Hole Adventure Golf, Bradenton Beach, the Historic Bridge Street Pier, and Bridge Street.
The two-bedroom, three-bathroom property sleeps six, boasts a fully equipped kitchen, terrace, garden, free Wi-Fi, and access to a tennis court; barbecue facilities are also available.
Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach - Longboat Key, FL
9.2 19 reviews
Longboat Key, FL
22/08 – 05/09
£216/nighttotal: £3024 (14 )

Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach

1 3
cottage , Bradenton Beach
Tradewind Resort #32, a self-catering property in Bradenton Beach, Florida, is situated a short drive from Mote Marine Laboratory & Aquarium and Cortez Beach.
This one-bedroom holiday home sleeps four guests and boasts a fully equipped kitchen, private patio, and access to a swimming pool and hot tub at the resort, alongside being close to local amenities.
Coastal Luxury 7mi To Anna Maria Private Cottage - Longboat Key, FL
10 7 reviews
Longboat Key, FL
26/12 – 31/12
£156/nighttotal: £780 (5 )

Coastal Luxury 7mi To Anna Maria Private Cottage

1 2
cottage , Bradenton
This Bradenton holiday home is conveniently located near LECOM Park and The Bishop Museum of Science and Nature (approx. 6.4 km to each), a short drive from Tampa Bay (approx. 24 km) and Lido Beach (approx. 71 km).
The self-catering property sleeps two guests in one bedroom and one bathroom, offering Wi-Fi, air conditioning, and is well-equipped for a comfortable stay near local attractions including the Mall at University Town Center and St. Armands Circle.

Frequently asked questions about cottages in Longboat Key, FL

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Handpicked Holiday Cottages with a Jacuzzi in Longboat Key, FL

Settle into a private hot tub at these waterside cottages in Longboat Key, FL for the ultimate coastal unwind.

Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included - Longboat Key, FL
10 12 reviews
Longboat Key, FL
22/08 – 05/09
£442/nighttotal: £6188 (14 )

Beautiful New Pool/spa, Steps To Sand & Restaurants, Golf Cart Included

2 3
cottage , Holmes Beach
This Holmes Beach seaside cottage, near Bradenton Beach, is a 10-minute walk from Island Gallery West and under 2km from both Holmes Beach and Manatee Public Beaches.
This 96 square metre holiday home sleeps six, boasting two bedrooms, one bathroom, a private pool, hot tub, barbecue, and fully equipped kitchen including a dishwasher; free Wi-Fi is also provided.
Bridge Street Beach House | Wi-fi | Center Of All - Longboat Key, FL
10 3 reviews
Longboat Key, FL
11/07 – 17/07
£350/nighttotal: £2100 (6 )

Bridge Street Beach House | Wi-fi | Center Of All

3 3
cottage , Bradenton Beach
This detached house is located in the Bridge Street district of Bradenton Beach, a short 500-metre walk from Bradenton Beach and the Anna Maria Sound Canal, and near amusement parks.
This 60 square metre holiday home accommodates up to six guests, offering three bedrooms, one bathroom, a kitchen with a fridge, microwave and dishwasher, air conditioning, a communal swimming pool, hot tub, garden, spa, tennis court, and on-site parking, with complimentary Wi-Fi and access to table tennis and billiards.

Browse Pet-Friendly Cottages in Longboat Key, FL

Book a dog-friendly cottage in Longboat Key, FL for a relaxing break that welcomes the whole family.

Cottage In The Shade, 3 Min Walk To Beach, Restaurants, And Pickleball Crt. - Longboat Key, FL
9.6 9 reviews
Longboat Key, FL
20/08 – 22/08
£240/nighttotal: £480 (2 )

Cottage In The Shade, 3 Min Walk To Beach, Restaurants, And Pickleball Crt.

2 2
cottage , Bradenton Beach
This holiday home offers a prime location in Bradenton Beach, just a 5-minute walk from Bradenton Beach and the historic Bridge Street Pier, enabling car-free exploration.
This two-bedroom bungalow accommodates up to four guests and features air conditioning, Wi-Fi, on-site parking, and a barbecue for outdoor cooking.
Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Longboat Key, FL
9.8 7 reviews
Longboat Key, FL
22/08 – 05/09
£252/nighttotal: £3528 (14 )

Cozy Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too

1 3
cottage , Bradenton Beach
This newly renovated 1-bedroom, 1-bathroom cottage in Bradenton Beach is just a few steps from Bradenton Beach and the community pool, offering easy access to local boutiques, Bridge Street Bistro, and Anna Maria Oyster Bar.
This 65 square meter holiday home accommodates up to four guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, Wi-Fi, and private parking, with the option to book an adjacent unit for larger groups.
Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool - Longboat Key, FL
10 10 reviews
Longboat Key, FL
20/08 – 22/08
£337/nighttotal: £674 (2 )

Cozy 1-bed Cottage In Adorable Tradewinds Bradenton Beach, Steps To Beach/pool

1 2
cottage , Bradenton Beach
This recently renovated one-bedroom holiday home in Bradenton Beach is located just a few steps from Bradenton Beach and the Gulf of Mexico, placing you within 500 meters of local boutiques and dining spots such as Bridge Street Bistro.
This 65 square meter holiday home accommodates up to four guests and features a fully equipped kitchen, air conditioning, Wi-Fi, a community swimming pool, and individual televisions in each room, with the option to book a neighbouring unit for larger groups.
115 M² Cottage ∙ 3 Bedrooms ∙ 6 Guests - Longboat Key, FL
8.0 1 review
Longboat Key, FL
01/07 – 08/07
£340/nighttotal: £2380 (7 )

115 M² Cottage ∙ 3 Bedrooms ∙ 6 Guests

3 2
cottage , Holmes Beach
The Seashell cottage is situated on a quiet street in Holmes Beach, just a short walk from the beach.
This pet-friendly three-bedroom property, spanning 114 square metres, offers comfortable furnishings and a garden, ideal for a family holiday.

Find the Best Seaside Cottages in Longboat Key, FL

Book a refreshing coastal getaway at comfortable shoreside cottages in Longboat Key, FL located near the beach.

Lou Lou's Hideaway: 1918 Historic Cottage In Cortez - Walk/bike To Ami Beaches - Longboat Key, FL
Longboat Key, FL
22/08 – 05/09
£177/nighttotal: £2478 (14 )

Lou Lou's Hideaway: 1918 Historic Cottage In Cortez - Walk/bike To Ami Beaches

1 3
cottage , Cortez

Compare Luxury Cottages in Longboat Key, FL

Discover a refined coastal retreat at a luxury cottage near the water in Longboat Key, FL.

The Cottage By Anna Maria Island - Longboat Key, FL
9.4 25 reviews
Longboat Key, FL
22/08 – 05/09
£94/nighttotal: £1316 (14 )

The Cottage By Anna Maria Island

3 3
cottage , Bradenton

Top-Rated Holiday Cottages with a Swimming Pool in Longboat Key, FL

Having an on-site pool alongside the beach makes every day at your Longboat Key, FL cottage feel special.

Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4 - Longboat Key, FL
10 2 reviews
Longboat Key, FL
22/08 – 05/09
£298/nighttotal: £4172 (14 )

Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4

2 3
cottage , Holmes Beach

Choose the Right Holiday Cottages with Free Parking in Longboat Key, FL

Forget parking stress with free on-site spaces included at these waterside cottages in Longboat Key, FL.

The Cottage By Anna Maria Island - Longboat Key, FL
9.4 25 reviews
Longboat Key, FL
22/08 – 05/09
£94/nighttotal: £1316 (14 )

The Cottage By Anna Maria Island

3 3
cottage , Bradenton

Search Holiday Cottages with Spa Facilities in Longboat Key, FL

Prioritise your well-being with exclusive spa facilities at these waterside cottages in Longboat Key, FL.

Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4 - Longboat Key, FL
10 2 reviews
Longboat Key, FL
22/08 – 05/09
£298/nighttotal: £4172 (14 )

Recently Renovated Luxury Ground Floor Island Home Close To Beach!o Sleeps 4

2 3
cottage , Holmes Beach
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