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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.

Casa Bonita

3 bd·3½ ba
5· 13

$3,249.00 USD total for 5 nights

Nov 29 – Dec 4, 2026

Amazing location, great host, and perfect for a family vacation!
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! ⭐⭐⭐⭐⭐
Taylor · Stay March 2026

Condo with a View on Longboat Key

0 bd·1 ba
4.98· 122

$971.80 USD total for 3 nights

Nov 20 – 23, 2026

Wonderful stay — great location, one of best views in Florida. Our host provided exceptional service
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!
L. S. · Stay April 2021

Heated Pool, Spa, BBQ, Games, Fire Pit, Sleeps 10

3 bd·2 ba
5· 75

$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!
A. · Stay August 2025

Luxury 2BR/2BA Condo Minutes from Beaches & IMG

2 bd·2 ba
5· 37

$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
C. · Stay February 2026

The Surof House

2 bd·1 ba
5· 2

$1,792.20 USD total for 3 nights

Nov 15 – 18, 2026

Beautiful house in a perfect location!
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!
Stay August 2025

Tropical Beach Condo!

1 bd·1 ba
5· 11

$994.40 USD total for 3 nights

Nov 20 – 23, 2026

Wonderful Vacation
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!
Stay June 2022

Condo With a View 4: On the Beach!

1 bd·1 ba
4.96· 26

$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!
S. · Stay July 2025

Ground Floor, Direct Oceanview on LBK!

0 bd·1 ba
5· 28

$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!
T. · Stay April 2025

Recommended Homes in Longboat Key

Handpicked properties we think you'll love in Longboat Key.

Panoramic Gulf View with Amazing Sunset.

1 bd·1 ba
4.87· 223

$1,227.18 USD total for 3 nights

Nov 29 – Dec 2, 2026

Turtle Crawl Inn 64

1 bd·1 ba
4.88· 73

$949.20 USD total for 3 nights

Nov 14 – 17, 2026

Turtle Crawl Inn 63

0 bd·1 ba
4.74· 88

$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

$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

Beach & Bay

7 bd·7 ba

$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.

Gulf Access

4 bd·4½ ba

$2,000.00 USD total for 3 nights

Nov 11 – 14, 2026

Perfect Sarasota Getaway:Close to all /Heated Pool

3 bd·2 ba
4.89· 18

$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.

Best for: luxury travelers, golf fans

Country Club Shores

Known for its waterfront properties, this area is perfect for boating and has easy access to Sarasota Bay.

Best for: families, boaters

Islandside

Home to the prestigious Longboat Key Golf Club, it offers beautiful beaches and upscale accommodation.

Best for: beach lovers, golfers

Longbeach Village

A charming historic neighborhood with quaint cottages and a vibrant arts scene. Don't miss the Mar Vista Dockside Restaurant.

Best for: culture seekers, foodies

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.

Best weatherNov – Apr

NovNow

78°F26°C

Rainfall Low

Demand Mid

Dec

73°F23°C

Rainfall Low

Demand Mid

Jan

71°F22°C

Rainfall Low

Demand Mid

Feb

73°F23°C

Rainfall Low

Demand Mid

Mar

76°F24°C

Rainfall Low

Demand Peak

Apr

81°F27°C

Rainfall Low

Demand Peak

May

86°F30°C

Rainfall Moderate

Demand Peak

Jun

89°F32°C

Rainfall High

Demand Peak

Jul

90°F32°C

Rainfall High

Demand Peak

Aug

90°F32°C

Rainfall High

Demand Peak

Sep

88°F31°C

Rainfall High

Demand Mid

Oct

84°F29°C

Rainfall Moderate

Demand Mid

Getting to and around Longboat Key

Reaching Longboat Key is easy from Sarasota-Bradenton Intl Airport, with convenient road access and local shuttles.

Airports
SARASOTA-BRADENTON INTERNATIONAL AIRPORT
Located 12 miles from Longboat Key, offering various domestic flights.
Driving
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.
Cycling
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.

Condo in Beachfront Resort with Heated Pool

1 bd·1 ba
5· 29

$563.87 USD total for 3 nights

Nov 29 – Dec 2, 2026

Hart's Paradise @ Barefoot Beach

1 bd·1 ba
4.77· 82

$562.00 USD total for 3 nights

Nov 21 – 24, 2026

Gorgeous Beach Home with heated pool

3 bd·3 ba
5· 9

$15,424.71 USD total for 28 nights

Nov 11 – Dec 9, 2026

Sun & Sand ~ “Happy Place Villa” Steps to Beach

2 bd·1 ba
5· 13

$1,525.50 USD $1,426.63 USD total for 5 nights

Nov 12 – 17, 2026

Tampa Event Compound, Hot Tub Bar

10 bd·10 ba
5· 48

$21,590.00 USD $18,426.50 USD total for 7 nights

Nov 11 – 18, 2026

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bd·1 ba
5· 2

$2,178.64 USD total for 7 nights

Nov 28 – Dec 5, 2026

Luxe Waterfront Home w/ PoolElevatorGulf Access

5 bd·4 ba
4.91· 11

$5,779.00 USD total for 6 nights

Nov 11 – 17, 2026

Funshine Sunset Beach - Steps from the beach!!

1 bd·1 ba
5· 142

$535.35 USD total for 3 nights

Nov 18 – 21, 2026

$553.11 USD total for 3 nights

Nov 22 – 25, 2026

Tampa 6BR Heated Pool HotTub,Theater,GameRoom,Gym

6 bd·3½ ba
5· 55

$5,989.00 USD $5,546.04 USD total for 3 nights

Nov 11 – 14, 2026

Craig House with Heated Pool

3 bd·2 ba
4.8· 107

$1,437.32 USD $1,376.50 USD total for 5 nights

Jan 14 – 19, 2027

Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub

3 bd·2 ba
5· 50

$1,780.00 USD total for 3 nights

Feb 23 – 26, 2027

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