
Holiday houses in Longboat Key
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Top-rated holiday rentals in Longboat Key
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Other great holiday rentals in Longboat Key
Guest favourite

Townhouse in Longboat Key
4.82 out of 5 average rating, 39 reviewsCedars Tennis -Gorgeous 2 bed, 3 level Townhouse
PaulaRating, 5 stars2 months ago
We spend a wonderful week at Laura's listing. The apartment was modern, clean, quiet and well furnished with all the necessaries. Laura was incredibly helpful and fast to respond with any questions we had before and during our stay. I would highly recommend this apartment for a beach holiday in sunny Florida!
Top Guest favourite

Home in Bradenton Beach
4.99 out of 5 average rating, 71 reviewsBeach front! Sunsets + Bridge Street+ Restaurants!
AmberRating, 5 stars2 days ago
Our family decided to go to Anna Maria Island to celebrate my oldest graduating high school. It was by far the best, most relaxing vacation we’ve had. Everything about the location, atmosphere, walking distance to the beach, and especially the home was perfect! Ashley was a great host, kind a responsive, and provided the exact replica of the picture perfect home you see listed. Thank you for this much needed slice of paradise. We will definitely be back!
Top Guest favourite

Home in Longboat Key
4.96 out of 5 average rating, 82 reviewsBeautiful Beach House
NicoleRating, 5 stars1 week ago
Randy’s house was perfect for the 5 of us and our dog. We got rained out one day, so the porches were a lovely place to listen to the storms. The beach access easy to find and amazing!!! It reminded me of summers here as a kid. We borrowed chairs from the house and spent hours with our feet in the water. Close to both Bradenton Beach and St. Armand’s for restaurants and shopping. Highly recommend Randy’s house!
Superhost

Condo in Longboat Key
4.88 out of 5 average rating, 32 reviews3 BR Condo On Longboat Key Beach and Waterfront
LouisRating, 5 stars1 week ago
What a wonderful property. The view is incredible. You are really right on top of the beach. The sound of the ocean while drinking my morning coffee will be something I dearly miss. This place is perfect for families ( really anyone) Our 2 year old son does not have beach stamina yet. No problem you are on a private beach. The apartment is a couple of minutes away ( even at toddler walking speed). We would bounce between the beach,apartment and pool in a matter of minutes. The apartment is stocked with everything you need. Shopping and restaurants are super close. Will, the host is top notch. Book this property with no hesitation ( if your lucky enough) We hope to go back.
Top Guest favourite

Apartment in Longboat Key
5 out of 5 average rating, 27 reviewsTurquoise Gem 1st Floor
KinsleyRating, 5 stars1 week ago
The turquoise gem is truly a gem, I’m so thankful we found this place! It’s very cozy & clean. Although, I would recommend bringing some slippers or wearing socks, I get why there’s not a lot of rugs (sand & such) but the floor isn’t the most comfortable walking around barefoot. The location is perfect, and super close to a convenient store & restaurants. The beach is gorgeous. Loved it here & we would totally stay again!☺️
Top Guest favourite

Tiny home in Bradenton
5 out of 5 average rating, 20 reviewsRomantic Luxe Tiny Home+ Hot Tub
LisaRating, 5 stars2 weeks ago
I can't say enough positive things about David & Tricia's home. Every detail was well thought out. Vegan snacks were left out for us to enjoy and the house was impeccably clean. The house and surrounding nature were beautiful and as described. We were greeted by 2 beautiful owls outside- what a blessing. The space is absolutely private, and adorable. The hosts were accommodating & Communicative. We wl definitely be back
Superhost

Home in Longboat Key
4.89 out of 5 average rating, 47 reviewsLBK Dreamin' Beach Bungalow
NewRating, 5 stars2 months ago
Cozy spot. Peaceful surroundings. Easy to walk to the beach or a few local restaurants. Nice pool and responsive hosts.
Top Guest favourite

Guesthouse in Bradenton
4.99 out of 5 average rating, 96 reviewsPrivate Stock Tank Pool. Cozy Tropical Stay
JordanRating, 5 stars1 week ago
Was a really nice & cozy place, definitely would come back !!.
Quick stats about holiday rentals in Longboat Key
Total rentals
890 properties
Nightly prices starting at
$50 NZD before taxes and fees
Total number of reviews
9.8K reviews
Family-friendly rentals
690 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
740 properties have a pool
Destinations to explore
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- House rentals Longboat Key
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- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
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- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park