Beachfront vacation rentals in Longboat Key

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Top-rated beachfront rentals in Longboat Key

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Guest favorite

Home in Longboat Key

4.87 out of 5 average rating, 106 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

Feb 28 – Mar 7

R10,880 ZAR per night

Guest favorite

Apartment in Siesta Key

4.99 out of 5 average rating, 142 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Beautiful Apartment w/ Hotel Services, at Siesta Key Beach. Totally remodeled. Fully equipped to spend the best holidays with family or friends. Condo hotel, on the best beach in Siesta. Beach pool, shade pool (heated), gym, 3 tennis courts on site (2 clay, 1 hard) and 2 pickle ball courts. Master bedroom with King bed. The Mattress is a SAATVA ORGANIC. 2nd room with 2 single beds, and a queen sofa bed, in the living room. Pack n Play 600 MB Wifi. HD TV. 70” Smart TV Nesspreso, Keurig Machines

Nov 16 – 23

R8,557 ZAR per night

Guest favorite

Apartment in Treasure Island

4.91 out of 5 average rating, 278 reviews

Attractive Beachfront Studio - Live Like a Local!

The true treasure of Treasure Island! Tucked right off of Gulf Blvd, on a secluded beach, this comfortable newly remodeled private studio is nestled on a lushly landscaped beachfront residential property with renters on-site. This cozy spot is all about barefoot luxury — you're just steps from the beach and biking or walking distance to laid back beach bars, live music & restaurants. Please note: There’s no guest parking available, but paid parking is nearby as well as a frequent public trolley.

Aug 10 – 17

R2,636 ZAR per night

Guest favorite

Apartment in Longboat Key

4.82 out of 5 average rating, 124 reviews

Ocean Front Studio Special From $99/night

This complex is a 2 story bldg with only 14 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures are taken from the condo, so what you see is what you get, direct beautiful Ocean views. Sip your beverage of choice as you enjoy the sunsets and the balmy breezes on your large walkout private patio with a table, chairs, chaise lounges which faces the aqua waters of the Gulf of Mexico. This is a condo that you will want to return to year after year.

Oct 22 – 29

R4,002 ZAR per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, 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!

Aug 17 – 24

R11,903 ZAR per night

Guest favorite

Home in Holmes Beach

4.95 out of 5 average rating, 158 reviews

Sea AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Nov 19 – 26

R5,271 ZAR per night

Guest favorite

Condo in Longboat Key

4.86 out of 5 average rating, 154 reviews

The Beach Condo Unit #107 Beachfront

Unit #107 has a private beach access, This end condo unit is quiet, ground floor and only steps to the white sand beach down a private path. . Note that this is a small studio, 330 sq. ft. with queen murphy bed and a queen sofa bed. It has no separate bedroom. Full view of gulf and sunsets. There are only 15 units in the complex, few people on beach or at the heated pool. No daily maid service. Only initial limited supply of products/soaps/towels. Common use W/D across from unit.

Jan 24 – 31

R6,180 ZAR per night

Guest favorite

Home in Longboat Key

4.9 out of 5 average rating, 105 reviews

Longboat Key Beach House

This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway and includes your beach supplies. A 3 minute walk to the beach and to the bay, this house is within a block of restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has 10 HarTru Tennis Courts, a junior Olympic POOL, gym, bicycle rental and tiki bar. Only Minutes to Holmes, Bradenton and Coquina Beaches.

Aug 17 – 24

R7,597 ZAR per night

Guest favorite

Apartment in Treasure Island

4.92 out of 5 average rating, 162 reviews

Treasure Island Beach Apartment #1

Location! Situated on Gulf Blvd, directly across from the 123rd Street beach access in Treasure Island. Walk to John's Pass for restaurants, shopping, bars and music, boat trips and fishing. Two bedroom, one bath private apartment, with all the amenities you need for a great beach vacation - beach chairs, umbrella, cooler, barbecue, bicycles. Master bedroom has queen bed, and Roku tv. Smaller bedroom has twin trundle bed, perfect for the kids. Full kitchen. Off street parking for one car.

Jan 7 – 14

R2,401 ZAR per night

Guest favorite

Condo in Longboat Key

4.93 out of 5 average rating, 144 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.

Dec 2 – 9

R5,805 ZAR per night

Guest favorite

Condo in Longboat Key

4.97 out of 5 average rating, 148 reviews

Charming Condo on the Coast!

This sublime oceanfront studio 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 studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with complimentary chairs and umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Apr 6 – 13

R5,969 ZAR per night

Guest favorite

Cottage in Bradenton Beach

4.99 out of 5 average rating, 124 reviews

Bradenton Beach Sunsets 2, 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.

Oct 1 – 8

R4,337 ZAR per night