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.
10 22 reviews
Longboat Key, FL
22/08 – 05/09
£366/nighttotal: £5124 (14 )
Palm Villa By Beach Boutique Rentals
2 3
cottage , Holmes Beach
This charming cottage is situated just a short walk from the beach path in Holmes Beach, offering easy access to the sand and nearby shops and restaurants. The cottage has consistently received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers. The two-bedroom cottage spans 75 square metres and comfortably accommodates up to five guests. It features a fully equipped kitchen, a private patio with outdoor shower, and a shared laundry facility, ensuring a relaxing and comfortable stay.
Longboat Key, FL
20/08 – 21/08
£327/nightfor 1 night
Lido Key Getaway - Bikes & Beach Gear
2 2
cottage , Sarasota
This detached house is located in Sarasota, 450 metres from Lido Beach and within walking distance of St. Armands Circle's shops and restaurants. This two-bedroom property accommodates up to four guests and features a private, heated swimming pool, a screened lanai, an outdoor shower, and complimentary beach equipment, with parking and air conditioning provided.
Longboat Key, FL
26/12 – 31/12
£605/nighttotal: £3025 (5 )
Castaway Cottage Near Img And Beaches
1 2
cottage , Bradenton
This detached house is located in Bradenton, 7 kilometres from the city centre and close to Blake Medical Center, offering free Wi-Fi and a barbecue area. This property accommodates two guests and includes a kitchen with a fridge, microwave oven, and dishwasher, alongside air conditioning and parking.
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.
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
This non-smoking holiday home in Bradenton Beach is a short walk from Canal Anna Maria Sound and Bradenton Beach, with Coquina Beach and Bean Point Beach nearby. This holiday home offers a private terrace, a fenced yard, complimentary Wi-Fi, air conditioning, a barbecue, laundry facilities, a full kitchen, and on-site parking, with opportunities for wildlife watching and birding tours in the vicinity.
Longboat Key, FL
22/08 – 05/09
£293/nighttotal: £4102 (14 )
Charming 1920s Cottage, Waterfront Just 50 Ft Away, Beach Just 1 Minute Stroll!
2 3
cottage , Bradenton Beach
This Bradenton Beach holiday home, a 1920s cottage on 7th Street South, enjoys a prime location less than 0.16km from the beach and a short distance from Bridge Street's shops and restaurants. The two-bedroom, one-bathroom property sleeps five, boasting a wraparound porch with stunning Bay views, new memory foam beds, a fully equipped kitchen, streaming TV, and proximity to attractions including the John and Mable Ringling Museum of Art and Mote Marine Laboratory & Aquarium.
10 3 reviews
Longboat Key, FL
22/08 – 05/09
£151/nighttotal: £2114 (14 )
Just Minutes From Our Beautiful Gulf Of Mexico Beaches & Stunning Sunsets !!
2 3
cottage , Cortez
This pet-friendly two-bedroom holiday home in Bradenton is located 3.2 kilometres from the Gulf of Mexico's beaches and 2.4 kilometres from the Historical Cortez Fishing Village. The 93 square metre holiday home accommodates up to four guests and features air conditioning, a kitchen with a fridge and microwave, and is conveniently situated for fishing charters, jet skiing, dolphin tours, and boating.
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.
10 26 reviews
Longboat Key, FL
22/08 – 05/09
£366/nighttotal: £5124 (14 )
Orchid Villa By Beach Boutique Rentals
2 3
cottage , Holmes Beach
This charming cottage is located in Holmes Beach, just a short walk from the beach path and within easy reach of shops and restaurants. It has consistently received excellent ratings for location, cleanliness and overall experience, making it a popular choice for travellers. The cottage is spread over 75 square metres and can accommodate up to 5 guests in its two bedrooms and two bathrooms. It offers a range of amenities including a fully equipped kitchen, air conditioning, a private patio and a shared laundry facility, ensuring a comfortable and enjoyable stay.
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.
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.
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.
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.
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.
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.
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
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.
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.
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.
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
When is the best time to rent a cottage in Longboat Key, FL?
The best time to rent a cottage on Longboat Key is during the shoulder seasons, from April to May and September to October. The weather is still pleasant, but the crowds are smaller and prices are lower. You'll have a more peaceful experience.
What are the can't-miss sights in Longboat Key, FL?
You can't miss the iconic St. Armands Circle, a vibrant shopping and dining district with a charming European feel. For a taste of nature, visit the Longboat Key Nature Center, a 42-acre preserve with diverse flora and fauna. And of course, no trip to Longboat Key is complete without spending time on the beautiful beaches, like the one at Longboat Key Club.
What are the best cottages with a pool in Longboat Key, FL?
Why consider renting a cottage in Longboat Key, FL for your stay?
Renting a cottage on Longboat Key offers a unique and intimate experience. You'll have more privacy and space than a hotel room, and often enjoy access to private beaches and gardens. Many cottages have a charming, homey feel, making you feel right at home.
What are the best cottages with a jacuzzi in Longboat Key, FL?
Can you easily explore Longboat Key, FL on foot or by bike?
Longboat Key is very walkable and bikeable, especially the south end. You can easily explore the shops, restaurants, and beaches without needing a car. There are also bike paths and walking trails throughout the island.
What are the best cottages for families and kids in Longboat Key, FL?
What are the best restaurants in Longboat Key, FL with nature views?
For breathtaking views of the Gulf of Mexico, try Mar Vista Dockside Restaurant, a local favourite for its fresh seafood and waterfront location. You can also enjoy a romantic dinner at Shore, known for its elegant atmosphere and stunning sunset views.
What are the best pet friendly cottages in Longboat Key, FL?
What family-friendly activities are available in Longboat Key, FL?
Longboat Key is a fantastic destination for families. You can enjoy a day of fun at the Mote Marine Laboratory & Aquarium, where you can learn about marine life and see fascinating creatures. For a more active day, rent kayaks or paddleboards and explore the calm waters of the Gulf of Mexico. And of course, building sandcastles and swimming on the beautiful beaches is always a hit with kids.
What are the best cottages with parking in Longboat Key, FL?
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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