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Beachfront vacation rentals in Longboat Key

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Top-rated beachfront rentals in Longboat Key

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Home

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

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

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

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

4.96 out of 5 average rating, 132 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

**No Kids allowed** Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, There is a pull-out large kitchen table. Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

Condo

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

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!

Cottage

4.96 out of 5 average rating, 161 reviews

Bradenton Beach Sunsets 3, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 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.

Condo

4.94 out of 5 average rating, 155 reviews

1 BR Beachfront Amazing sunsets-

Our condo is directly on the beach!! It is close to restaurants and dining, mini-golf, Clearwater and St. Pete's Beach. About 25 miles from Tampa, Florida for the Buccaneers NFL football and Lightning NHL hockey! We are about 37 miles from Busch Gardens. Only 95 miles to Disney World in Orlando! Mini-golf right across the street! You’ll love my place because of the neighborhood. My place is good for couples, small families, solo adventurers, and business travelers.

Island

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!

Serviced apartment

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

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Longboat Key beachfront rentals

Free parking on premises

Air conditioning

Beachfront home rentals with a pool

Rental unit

4.83 out of 5 average rating, 103 reviews

Parker Manor Apartment

Condo

4.93 out of 5 average rating, 104 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

Condo

4.96 out of 5 average rating, 112 reviews

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

Home

4.98 out of 5 average rating, 44 reviews

Ready to Host! Anna Maria Chateau. Private Pool!

Condo

4.94 out of 5 average rating, 190 reviews

Siesta key getaway!

Condo

5 out of 5 average rating, 21 reviews

Breathtaking Beachfront Views in Siesta Key

Bungalow

4.89 out of 5 average rating, 186 reviews

Private Beach Bungalow 1BR *Heated POOL**PETS ok

Condo

5 out of 5 average rating, 27 reviews

AMI Perfect Experience

Beachfront home rentals with a hot tub

Home

4.95 out of 5 average rating, 274 reviews

Ready to go! Heated Pool/Hot Tub Luxury Home

Condo

4.97 out of 5 average rating, 114 reviews

Siesta Key For Me @ The Palm Bay Club

Condo

4.91 out of 5 average rating, 126 reviews

Beach Condo with water view!

Condo

4.88 out of 5 average rating, 141 reviews

Sun, Beach Views, and Smiles!!!

Condo

4.84 out of 5 average rating, 214 reviews

Gulf Strand Beach Resort

Condo

4.96 out of 5 average rating, 169 reviews

Sea La Vie- Studio by the bay!

Condo

5 out of 5 average rating, 29 reviews

Cozy Island Oasis! Prime location+Pool+Jacuzzi!

Home

5 out of 5 average rating, 14 reviews

Pineapple Paradise! 1 block to Beaches!

Pet-friendly beachfront home rentals

Cottage

4.8 out of 5 average rating, 258 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Townhouse

4.94 out of 5 average rating, 108 reviews

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U2 ♥

Home

4.85 out of 5 average rating, 109 reviews

Open Water Home Bring your boat! No storm issues.

Bungalow

4.99 out of 5 average rating, 186 reviews

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Rental unit

4.94 out of 5 average rating, 142 reviews

Vintage Florida Beach Efficiency

Condo

4.82 out of 5 average rating, 153 reviews

Beach Studio 5

Condo

4.91 out of 5 average rating, 105 reviews

Waterside Studio in the heart of TI, walk to beach

Villa

4.91 out of 5 average rating, 152 reviews

Mermaid Villa Ocean Front!

Quick stats about beachfront rentals in Longboat Key

Total rentals
140 properties
Nightly prices starting at
€ 57 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