Longboat Key vacation rentals
Vacation rentals in Longboat Key by owner — compare homes, condos and cabins, message verified hosts and book direct. See every charge before you pay.
Longboat Key, stretching between Sarasota Bay and the Gulf, offers serene beaches at Coquina Beach and outdoor activities at Bayfront Park. Visitors come for deep-sea fishing charters, elegant dining at Saint Armands Circle, and the conservation trails at Joan Durante Park. Houfy allows direct booking with local hosts here, so you deal with the host from enquiry to check-in. Choose from beachfront estates, upscale condos, and cozy cottages near Anna Maria Island and Lido Key. With fewer rainy days, winter months see larger crowds and higher demand for rentals.
Top-Rated Vacation Homes in Longboat Key
Browse the highest rated vacation properties in Longboat Key.
$3,249.00 USD total for 5 nights
Nov 29 – Dec 4, 2026
We had the most amazing stay at this beautiful house in Bradenton Beach for our family vacation! From the moment we arrived, everything exceeded our expectations. The home was clean, well decorated, and incredibly comfortable for a family vacation with kids — it truly felt like a home away from home. 🌴☀️ The location couldn’t have been better. It was an easy walk to the beach, and we loved being so close to Bridge St. The house itself was perfect for a family trip — plenty of space to spread out, a well-stocked kitchen, and great areas to hang out together after long days in the sun. The outdoor space was a huge highlight too — we had SO much fun in the pool! Kelly clearly put a lot of care into the property. Communication was smooth, check-in was easy, and she thought of all the little details that make a stay special. We made so many great memories here and would absolutely stay again. If you’re looking for the perfect spot for a relaxing beach getaway with family, this place is a total gem. Highly recommend! ⭐⭐⭐⭐⭐
$971.80 USD total for 3 nights
Nov 20 – 23, 2026
My wife and I stayed here for a few days and loved it. The room was clean, with fresh sheets/towels. The view is spectacular. One of the best in Florida. Whether you’re on the balcony or the beach, you’re sure to get a perfect view of the ocean. There is also a little coffee shop just a few minute walk away, and several excellent seafood restaurants within a 10 minute drive + a publix! Our host, Heidi, went above and beyond. She ensured our check in, stay, and checkout was smooth. We had zero issues. I wish every host I’ve had was like Heidi! We were even given a little wedding gift (this was our honeymoon). She was very responsive by text to answer any questions. Our days consisted of mornings on the balcony, afternoons on the beach, a post beach cigar at sunset (Heidi even called the property management to make sure smoking was allowed on the balcony), and going out for dinner. Everything you could ask for. Overall, I highly recommend staying here if you’re looking to unwind, or just simply get away for a few days. Hope to be back soon!
$637.00 USD total for 3 nights
Nov 15 – 18, 2026
We have nothing but good things to say about this place and we will definitely be returning! Everything listed in the description was accurate even the photos! Our teenage boys definitely enjoyed the PS4 and everyone enjoyed the pool/spa in backyard! One of the favorite things was the Welcome binder left from the host with clear instructions, recommendations of things to do in the area, information about the house, etc. It was so organized and detailed! We felt so at home with this place and the layout is perfect, we didn’t feel on top of each other. There’s so much space so everyone! Ryan is a great host, if you had any questions, he was quick to respond! Highly recommend booking this place especially if traveling with family/kiddos!
$517.36 USD total for 3 nights
Nov 15 – 18, 2026
My husband and I stayed for 5 weeks and absolutely loved it! We will definitely go back. It is a new favourite! Here are all the reasons we enjoyed our extended stay: - Mike is an outstanding host - The condo is modern, newly renovated and beautifully decorated (even better than the pictures show) - Clean, spacious with high ceilings and quiet - Beautiful view of the pond from the screened in balcony - We met a wonderful group of people for drop-in pickleball every morning - Met a group who played Mah Jongg at the Club House - Lending library at the Club House - Walking distance to Publix - Close to beautiful beaches - Close to GT Bray, a sports, recreation and fitness centre
$1,792.20 USD total for 3 nights
Nov 15 – 18, 2026
A beautiful beach house in a prime location! Within walking distance to restaurants and shops! The house has everything you can think of for a relaxing stay! From beach supplies and towels to the outdoor shower, outdoor swing, a grill and full kitchen inside. The views are stunning from all the rooms and it has a beautiful wrap around deck for sunset! I would highly recommend staying here! I will be back!
$994.40 USD total for 3 nights
Nov 20 – 23, 2026
If you’re thinking of booking this property, do it! You have beautiful views of the gulf. Steps away from the pool and beach. Beach was not crowded at all. We saw dolphins and manatees swim by! The condo is beautiful and spacious! The couch has a sleeper sofa for our son. Heidi is a wonderful host who truly makes you feel welcome! We will definitely be back!
$994.40 USD total for 3 nights
Nov 11 – 14, 2026
We had a great stay for our family babymoon! The condo was clean, easy to find, quiet, and just steps from the beach. The view from the 2nd floor balcony was beautiful, and the amenities were exactly as described. Our kids (8 & 4) slept comfortably on the pull-out couch, and the bed was perfectly firm for us. If you’re a shorter pregnant mama (like me at 5’2”), bring a stool to get on the bed. It’s no big deal if you’re prepared! We loved having both beach and pool access, plus nearby beaches and restaurants to explore on the island and mainland. Heidi was a great host! She was very responsive and thoughtful. We arrived late, and she dropped off some treats for us to find, which was a kind touch. We’d definitely stay here again!
$971.80 USD total for 3 nights
Nov 11 – 14, 2026
I had a wonderful stay at Heidi’s condo on Longboat Key! The condo was very clean, the bed and pillows were comfy, and it was decorated with a cheery beach theme. The condo had everything I needed to make my 4 night stay enjoyable and comfortable like dishes, cooking pans, toaster, coffee maker, cooking oil, paper towels, plenty of toilet paper, and bath and beach towels. I enjoyed lots of meals, sipping my coffee, and also reading a book out on the little patio while I enjoyed the ocean view and hearing the waves. You can walk down to the beach in less than a minute and what a beautiful beach it is. The location of the condo is a great spot in LBK with quick access to restaurants, grocery stores, and shopping areas, and I especially like that it’s not a heavily touristy area. Heidi herself made my stay special by bringing me some goodies on my first morning and checking in with me a few times during my stay. She is by far the best Airbnb host I’ve ever stayed with. I’ll be back!
Recommended Homes in Longboat Key
Handpicked properties we think you'll love in Longboat Key.
$1,227.18 USD total for 3 nights
Nov 29 – Dec 2, 2026
$949.20 USD total for 3 nights
Nov 14 – 17, 2026
$838.46 USD total for 3 nights
Nov 11 – 14, 2026
$1,493.86 USD $1,430.46 USD total for 3 nights
Dec 11 – 14, 2026
Sleeps 20 • Heated Pool • Hot Tub • Outdoor Kitchen/Theater
$2,875.04 USD total for 3 nights
Nov 11 – 14, 2026
$25,878.00 USD total for 120 nights
Nov 11, 2026 – Mar 11, 2027
$8,425.50 USD total for 60 nights
Nov 11, 2026 – Jan 10, 2027
$6,403.51 USD total for 4 nights
Nov 15 – 19, 2026
Vacation houses with pools in Longboat Key
Cool off in style with these amazing pool homes in Longboat Key.
$2,000.00 USD total for 3 nights
Nov 11 – 14, 2026
$1,406.85 USD total for 3 nights
Nov 11 – 14, 2026
Pet friendly vacation rentals in Longboat Key
Bring your furry friend along! Browse pet-welcoming homes in Longboat Key.
$12,700.00 USD total for 182 nights
Nov 11, 2026 – May 12, 2027
Why visit Longboat Key
Discover what makes Longboat Key a perfect vacation rental destination.
Pristine Beaches
Long stretches of white sand await you
Visit the stunning Coquina Beach, just 10 miles south, known for its powdery sand and vibrant sunsets. Perfect for sunbathing, picnicking, or simply relaxing.
Lush Mangrove Tunnels
Kayak through natural wonders
Explore the magical mangrove tunnels in the nearby Robinson Preserve, only 15 miles away. Ideal for kayaking, you might spot dolphins and manatees along the way.
Rich Local History
Discover Longboat Key's past
Visit the Longboat Key Historical Society, just minutes away, to learn about the island's intriguing heritage and its early settlers.
Delectable Seafood
Savor fresh, local flavors
Indulge at Chart House, famed for its locally sourced seafood, located just 2 miles from the city center. Don't miss their famous clam chowder.
Where to stay in Longboat Key
The best areas and neighborhoods for your vacation rental in Longboat Key.
Bay Isles
A secure gated community, offering boating access and the Longboat Key Club for golf and tennis enthusiasts.
Country Club Shores
Known for its waterfront properties, this area is perfect for boating and has easy access to Sarasota Bay.
Islandside
Home to the prestigious Longboat Key Golf Club, it offers beautiful beaches and upscale accommodation.
Longbeach Village
A charming historic neighborhood with quaint cottages and a vibrant arts scene. Don't miss the Mar Vista Dockside Restaurant.
Find Longboat Key vacation rentals that suit your style
Condos, vacation homes, villas and more — pick the kind of Longboat Key vacation rental you want, then book it direct with the host.
Longboat Key vacation rentals with free WiFi, hot tub or air conditioning
Free WiFi, hot tub, air conditioning and more — every Longboat Key vacation rental here is listed by a verified host and bookable direct, with the price the host set.
Top attractions in Longboat Key
All within driving distance of Longboat Key vacation rentals.
Coquina Beach
Known for its white sand and turquoise waters, ideal for families. · 10 miles
Robinson Preserve
A beautiful nature reserve offering walking trails and kayaking opportunities. · 15 miles
Mote Marine Laboratory & Aquarium
Discover marine life exhibits just 6 miles away. · 6 miles
Euphemia Haye Restaurant
Celebrated for its unique blend of traditional and contemporary cuisine. · 3 miles
The Ringling Museum
Featuring an extensive art and circus history collection, only 12 miles away. · 12 miles
Longboat Key Golf Club
Offers two exceptional golf courses with stunning views. · 2 miles
Best Time to Visit Longboat Key
Enjoy sunny days on Longboat Key with mild winters and warm summers. Best months to visit are November to April, with highs from 70°F to 85°F.
The best time to visit Longboat Key is November to April, when the weather is at its best.
Getting to and around Longboat Key
Reaching Longboat Key is easy from Sarasota-Bradenton Intl Airport, with convenient road access and local shuttles.
- SARASOTA-BRADENTON INTERNATIONAL AIRPORT
- Located 12 miles from Longboat Key, offering various domestic flights.
- RENTAL CAR
- Available at Sarasota Airport, providing flexibility to explore the island at your own pace.
- TAXI & RIDESHARE
- Taxis and services like Uber and Lyft are readily available throughout the area.
- BIKE RENTALS
- Rent bikes locally, with dedicated lanes making it easy to explore the scenic beaches.
Similar vacation rentals near Longboat Key
Homes within 60 miles of Longboat Key, from verified hosts.
$563.87 USD total for 3 nights
Nov 29 – Dec 2, 2026
$562.00 USD total for 3 nights
Nov 21 – 24, 2026
$15,424.71 USD total for 28 nights
Nov 11 – Dec 9, 2026
$1,525.50 USD $1,426.63 USD total for 5 nights
Nov 12 – 17, 2026
$21,590.00 USD $18,426.50 USD total for 7 nights
Nov 11 – 18, 2026
$2,178.64 USD total for 7 nights
Nov 28 – Dec 5, 2026
$5,779.00 USD total for 6 nights
Nov 11 – 17, 2026
$535.35 USD total for 3 nights
Nov 18 – 21, 2026
Funshine Pointe Capri - Newly Renovated - Intercoastal Views
$553.11 USD total for 3 nights
Nov 22 – 25, 2026
$5,989.00 USD $5,546.04 USD total for 3 nights
Nov 11 – 14, 2026
$1,437.32 USD $1,376.50 USD total for 5 nights
Jan 14 – 19, 2027
$1,780.00 USD total for 3 nights
Feb 23 – 26, 2027
Explore near Longboat Key
Cities and towns within driving distance of Longboat Key, each bookable direct with the host.
Why guests book on Houfy
Direct with the host
Message the host before you book. Ask questions, confirm details, and deal with the person who owns the property.
Verified hosts
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Itemised pricing
Every charge is shown before you pay — including the API connection fee, where one applies.
More vacation rental destinations around Longboat Key
Frequently asked questions
Quick answers about booking vacation rentals in Longboat Key and what direct booking on Houfy actually means.
The best time to visit is from December to May when the weather is dry and pleasant, perfect for outdoor activities.
Yes, many rentals on Longboat Key welcome pets, but it's best to check with individual property listings for specific policies.
Bay Isles for luxury, Country Club Shores for boating, and Longbeach Village for cultural experiences are top choices.
Rentals often provide more spacious accommodations and amenities like kitchens, ideal for families or longer stays.
Options range from beachfront condos to spacious villas, catering to both budget-conscious travelers and luxury seekers.
Don't miss the fresh seafood, especially stone crab claws, a local delicacy often served at area restaurants.
Rental prices vary widely, ranging from $150 per night for a basic condo to over $1,000 for a luxury beachfront home.
Houfy is a platform that lets you book vacation rentals directly with the owner.
Yes, Houfy offers secure direct booking, allowing you to pay the listed price directly.































































































































































