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Beachfront vacation rentals in Longboat Key

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Top-rated beachfront rentals in Longboat Key

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Home in Longboat Key

4.86 out of 5 average rating, 110 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Condo in Indian Shores

4.99 out of 5 average rating, 108 reviews

Tropical Beachfront Penthouse-Beach Cottages II

Welcome to this spacious top floor oceanfront condo, located in beautiful Indian Shores, between Clearwater & St Pete Beach on the crystal clear waters of the Gulf of Mexico. This exquisite condo with magnificent oceanfront views is just fabulous! We've taken great care to ensure everything about this vacation home is remarkable & tastefully complimented with King & Queen size beds, full kitchen/dining/bar area, Free High Speed Internet, Premium TV, Garage Parking, Private Beach, and Pool/Spa.

Condo in Siesta Key

4.96 out of 5 average rating, 296 reviews

WE ARE OPEN—On the Beach; Siesta Key SunBum Studio

WE ARE OPEN POST OCT STORMS :) Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

Condo in Bradenton Beach

4.91 out of 5 average rating, 150 reviews

Beachfront condo in paradise open after the storms

Stop searching you found your beachfront vacation. No sitting in traffic for 90 minutes to get over the drawbridge to Anna Maria Island and looking to park for $20 an hour. You only have to go down 14 stairs from your second-floor condo to have your toes in the powder soft sand. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the beach. One of the best values on AMI as featured by trip101 article in pics 2&3

Condo in Longboat Key

4.91 out of 5 average rating, 160 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Condo in Longboat Key

4.99 out of 5 average rating, 112 reviews

Silver Sands - Winter Availability!

This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

Guesthouse in Bradenton Beach

5 out of 5 average rating, 148 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Island in Sarasota

4.97 out of 5 average rating, 317 reviews

New NOV Openings! Sarasota #1 Lux BEACH Villa

BOOK 2024 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Condo in Siesta Key

4.94 out of 5 average rating, 190 reviews

Siesta key getaway!

perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

Serviced apartment in Siesta Key

4.99 out of 5 average rating, 167 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

BEST SPOT AT SIESTA KEY BEACH. Beautiful apartment in Siesta Key Beach. Fully equipped. Condo hotel, on the best area of the beach in Siesta. Main bedroom with King bed. 2nd room with two single beds. Queen sofa bed in the living room. Pack n Play & high chair for children. 1200 MB Wifi. 70” Smart TV, 2 55” TVs Nesspreso, Keurig.

Condo in Bradenton Beach

4.99 out of 5 average rating, 114 reviews

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

An unforgettable experience awaits you at this getaway apartment right on the white sand beaches of Anna Maria Island. Wake up every morning to the best views of the turquoise waves of the Gulf of Mexico and spend your days enjoying the warm waters, filling your Instagram feed with dolphin pictures and dramatic sunsets.

Cottage in Sarasota

4.86 out of 5 average rating, 173 reviews

Heated Pool! Beach! Drift Inn Unit B Siesta Key!

Come and enjoy all that Unit B has to offer! This is a cottage style condo, very comfortable and inviting, fully equipped with your beach vacation in mind. The soft white quartz sands of Crescent Beach on Siesta Key are just a 3 minute walk from the cottage door. So is our lovely, saltwater heated pool.

Vacation rentals for every style

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Quaint homes, peaceful surroundings

Popular amenities for Longboat Key beachfront rentals

Free parking on premises

Air conditioning

Beachfront home rentals with a pool

Loft in Longboat Key

4.6 out of 5 average rating, 5 reviews

Inn on the Beach Beachfront Studio

Condo in Siesta Key

4.83 out of 5 average rating, 209 reviews

No Damage: Cozy 1BR Beach Condo on Siesta Key!

Condo in Siesta Key

4.96 out of 5 average rating, 112 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Cottage in Lido Key

4.84 out of 5 average rating, 111 reviews

Walk to Beach & St. Armands/Private cottage &grill

Condo in Sarasota

5 out of 5 average rating, 21 reviews

Breathtaking Beachfront Views in Siesta Key

Bungalow in Holmes Beach

4.89 out of 5 average rating, 18 reviews

Pirate's Den Bungalow steps from Beach Access!

Home in Indian Rocks Beach

4.98 out of 5 average rating, 119 reviews

Beachfront Bungalow w/ Pool & Hot Tub in IRB

Condo in Bradenton Beach

5 out of 5 average rating, 27 reviews

AMI Perfect Experience

Beachfront home rentals with a hot tub

Condo in Siesta Key

4.97 out of 5 average rating, 114 reviews

Siesta Key For Me @ The Palm Bay Club

Home in Seminole

4.95 out of 5 average rating, 274 reviews

Ready to go! Heated Pool/Hot Tub Luxury Home

Condo in Saint Pete Beach

4.88 out of 5 average rating, 141 reviews

Sun, Beach Views, and Smiles!!!

Condo in Ruskin

4.91 out of 5 average rating, 126 reviews

Beach Condo with water view!

Condo in Saint Pete Beach

4.84 out of 5 average rating, 214 reviews

Gulf Strand Beach Resort

Condo in St. Petersburg

4.96 out of 5 average rating, 169 reviews

Sea La Vie- Studio by the bay!

Home in Holmes Beach

4.95 out of 5 average rating, 94 reviews

The Peachy Beach House, steps to the gulf

Condo in Bradenton Beach

4.89 out of 5 average rating, 38 reviews

Gorgeous Gulf Views - Beachfront 2BR/2B Condo

Pet-friendly beachfront home rentals

Townhouse in Indian Rocks Beach

4.94 out of 5 average rating, 108 reviews

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U2 ♥

Cottage in Pass-a-Grille Beach

4.8 out of 5 average rating, 258 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Home in Ellenton

4.85 out of 5 average rating, 109 reviews

Open Water Home Bring your boat! No storm issues.

Bungalow in Indian Shores

4.99 out of 5 average rating, 186 reviews

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Rental unit in Indian Rocks Beach

4.94 out of 5 average rating, 142 reviews

Vintage Florida Beach Efficiency

Condo in Redington Shores

4.82 out of 5 average rating, 153 reviews

Beach Studio 5

Condo in Treasure Island

4.91 out of 5 average rating, 105 reviews

Waterside Studio in the heart of TI, walk to beach

Condo in Clearwater Beach

4.9 out of 5 average rating, 304 reviews

Amazing views on beachfront

Quick stats about beachfront rentals in Longboat Key

Total rentals
140 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
2.2K reviews
Family-friendly rentals
110 properties are a good fit for families
Rentals with a pool
130 properties have a pool
Rentals with dedicated workspaces
60 properties have a dedicated workspace

Destinations to explore