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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.

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
This Holmes Beach holiday home is a five-minute walk from Island Gallery West and Bradenton Beach, with Holmes Beach and Manatee Public Beach within a 2.4km radius.
Sleeping four guests in two bedrooms and three bathrooms, this self-catering property boasts a private pool, barbecue facilities, and a fully equipped kitchen including a dishwasher; DVD player and free Wi-Fi are also available.
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.
The Cottage By Anna Maria Island - Longboat Key, FL
9.4 25 reviews
Longboat Key, FL
26/12 – 31/12
£159/nighttotal: £795 (5 )

The Cottage By Anna Maria Island

3 2
cottage , Bradenton
This charming cottage is located in central Bradenton, within easy walking distance of restaurants, the Farmers Market, Village of the Arts, and the Riverwalk. It has consistently received excellent guest ratings.
This cosy home has three bedrooms and one bathroom, comfortably accommodating up to six guests. The cottage offers a fully equipped kitchen, a comfortable bathroom, air conditioning, a jacuzzi, and two porches, perfect for relaxing and enjoying the Florida sunshine.
Anna Maria Cottage With Golf Cart - Longboat Key, FL
10 23 reviews
Longboat Key, FL
22/08 – 05/09
£290/nighttotal: £4060 (14 )

Anna Maria Cottage With Golf Cart

2 3
cottage , Holmes Beach
This Holmes Beach holiday home is situated on the quiet north end of Anna Maria Island, within walking or cycling distance of local shops and the free island trolley, offering easy access to beaches and restaurants.
The single-storey property sleeps four guests in two bedrooms and one bathroom, and features an open-plan layout, a furnished patio, a barbecue, and includes beach chairs, umbrellas, and a two-person kayak for guest use; a golf cart is also provided.

Best Longboat Key, FL cottages with a garden

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
This historic 1918 fisherman's cottage is located in Cortez Village, a preserved fishing community, just 640 metres from Sarasota Bay and a 1.6 kilometre walk or 800 metre bike ride from the beaches of Anna Maria Island.
This 52 square metre holiday home offers accommodation for four guests, featuring one bedroom and one bathroom, with amenities including air conditioning, a kitchen with a fridge, microwave, and dishwasher, a garden, parking, and complimentary beach gear and bicycles.
Cottage On The Canal - Longboat Key, FL
10 5 reviews
Longboat Key, FL
26/12 – 31/12
£245/nighttotal: £1225 (5 )

Cottage On The Canal

1 2
cottage , Bayshore Gardens
This Bayshore Gardens flat offers direct canal access with boat docking potential, situated conveniently within 10 kilometres of Sarasota/Bradenton International Airport and close to Anna Maria Island, St Armand's Circle, and downtown Sarasota.
This 3-bedroom, 2-bathroom residence accommodates up to 6 guests and features a private garden with a swimming pool, a sun-drenched lanai with a bar, and a kitchen equipped with a fridge, microwave, and dishwasher, alongside air conditioning and internet.
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.
Tortuga Cottage · 1915 · Pool · Pet-friendly - Longboat Key, FL
9.6 4 reviews
Longboat Key, FL
26/12 – 31/12
£684/nighttotal: £3420 (5 )

Tortuga Cottage · 1915 · Pool · Pet-friendly

2 2
cottage , Bradenton Beach
This restored 1915 holiday home in Bradenton Beach is situated 176 metres from the Gulf of Mexico and 52 metres from Anna Maria Sound, with Bridge Street's dining and entertainment a four-minute walk away.
This three-bedroom, two-bathroom holiday home accommodates six guests and offers a private heated swimming pool, a screened porch, and is pet-friendly for dogs up to 18 kilograms.

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.

Bridge Street Beach House | Wi-fi | Center Of All - Longboat Key, FL
10 3 reviews
Longboat Key, FL
19/06 – 26/06
£316/nighttotal: £2212 (7 )

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

3 2
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.

Cozy Cottage Retreat At Tradewind Resort #32 In Bradenton Beach - Longboat Key, FL
9.2 19 reviews
Longboat Key, FL
11/07 – 17/07
£254/nighttotal: £1524 (6 )

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.
Charming Ground Level Resort Style 3 Units Condo  Of A Triplex- Unit A - Longboat Key, FL
10 29 reviews
Longboat Key, FL
22/08 – 05/09
£304/nighttotal: £4256 (14 )

Charming Ground Level Resort Style 3 Units Condo Of A Triplex- Unit A

2 3
cottage , Holmes Beach
This charming three-unit condo is located in Bradenton Beach, a short 15-minute drive from Holmes Beach and Manatee Public Beach. The property has received excellent user ratings and is a popular choice for travellers seeking a relaxing beach getaway.
The ground-floor unit offers 92 square metres of space and can comfortably accommodate up to six guests. Guests can enjoy a private pool, a fully equipped kitchen, a terrace, and a garden.
Romantic, Cute Cottage On Anna Maria Island. Close To Everything. Pet Friendly! - Longboat Key, FL
10 23 reviews
Longboat Key, FL
19/06 – 26/06
£374/nighttotal: £2618 (7 )

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

2 2
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 Beachside Cottage At Tradewinds/1br/pool/steps To Beach.unit1 Available Too - Longboat Key, FL
9.8 7 reviews
Longboat Key, FL
26/12 – 31/12
£296/nighttotal: £1480 (5 )

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

1 2
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.

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.

Castaway Cottage Near Img And Beaches - Longboat Key, FL
Longboat Key, FL
26/12 – 31/12
£605/nighttotal: £3025 (5 )

Castaway Cottage Near Img And Beaches

1 2
cottage , Bradenton

Compare Luxury Cottages in Longboat Key, FL

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

Castaway Cottage Near Img And Beaches - Longboat Key, FL
Longboat Key, FL
26/12 – 31/12
£605/nighttotal: £3025 (5 )

Castaway Cottage Near Img And Beaches

1 2
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.

Cottage In The Shade, 3 Min Walk To Beach, Restaurants, And Pickleball Crt. - Longboat Key, FL
9.6 9 reviews
Longboat Key, FL
22/08 – 05/09
£204/nighttotal: £2856 (14 )

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

2 3
cottage , Bradenton 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 Pelicans Nest  Cozy Stay Near The Beach - Longboat Key, FL
10 5 reviews
Longboat Key, FL
11/07 – 17/07
£266/nighttotal: £1596 (6 )

The Pelicans Nest Cozy Stay Near The Beach

2 3
cottage , Bradenton Beach

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.

Stay At Pine Key- A Cozy Beach Cottage Retreat! - Longboat Key, FL
Longboat Key, FL
11/07 – 17/07
£362/nighttotal: £2172 (6 )

Stay At Pine Key- A Cozy Beach Cottage Retreat!

2 3
cottage , Bradenton Beach
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