Holiday houses in Longboat Key

5 out of 5 average rating, 191 reviews

Apartment in Sarasota

Modern Luxury Apartment in a House Near Siesta

Large modern construction 950 square foot 1 bedroom apartment. Beautifully furnished, efficient apartment attached to the side of the main house. This unit has a private entrance with bright, modern interior and high ceilings. The apartment offers 1 King bed. The full bathroom has a large shower. A Washer and dryer located inside the apartment. Nestled on a quiet street with easy access to Siesta key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key. Great location!

Apartment in Longboat Key

4.95 out of 5 average rating, 103 reviews

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

4.87 out of 5 average rating, 97 reviews

Beautiful Panoramic Gulf and Sunset Views.

Beachfront Bliss — No Streets to Cross, Just Steps from the Sand! Enjoy breathtaking Gulf and sunset views from your private balcony in this spacious, newly updated condo. Featuring a brand-new bathroom and new flooring throughout, this 4th-floor unit (with elevator access) is the perfect retreat for your Longboat Key escape. The condo comfortably sleeps up to 6 guests. Sip your morning coffee or catch dolphin sightings and stunning sunsets from the balcony with 180° view of the Gulf. Elevator.

Guest suite in Indian Beach-Sapphire Shores

4.98 out of 5 average rating, 231 reviews

The Sapphire Suite 1Bed/1Bath

Beautifully elegant suite with a relaxing touch. A pleasant mix of Hispanic and Modern decor in a newly renovated living area complete with all necessities such as wifi, an outdoor patio and your own free parking. The suite is located MINUTES away from all of Sarasota's famous hotspots! It is down the street from Jungle Gardens. A 10minute walk to The Ringling Museum. 10minute drive to Downtown, 15 minute drive to both Siesta Key and St. Armand's Circle. It could not be located more ideally!

4.8 out of 5 average rating, 104 reviews

Gulfront Views! BEACHFRONT BARGAIN HUNT NOMINATED

THIS UNIT WAS NOMINATED TO BE FEATURED ON BEACHFRONT BARGAIN HUNT! Unit #102 Features: Full-size kitchen and Gulf-front views Bedding: 1 Queen Murphy Bed and a Sleeper Sofa Savor warm Gulf breezes while resting lavishly in this Gulf-front condo complex. Located directly on the beach, this resort features beautiful Gulf-front views. You are only steps from the white-sand beaches, placid turquoise waters and beautiful sunsets that will have you daydreaming about your next beach vacation.

4.99 out of 5 average rating, 137 reviews

Condo with a View 2: Beachfront!

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 in Bradenton Beach

4.97 out of 5 average rating, 190 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.

4.98 out of 5 average rating, 122 reviews

Condo in Bradenton

KING Bed + AMI Beaches!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

Apartment in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 140 reviews

Free Early Chk-in, Super Clean, Free Parking,Bikes

Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb property on the main road 1 mile from downtown Sarasota. Discover over 60 enticing amenities, from a secure room safe to a luxurious, indulgent bed. Just a stone's throw away from downtown Sarasota, Lido Beach, and essential amenities like grocery stores and pharmacies, our corner apartment with a dazzling wrap-around patio is your perfect hideaway. Bicycles at your disposal. Book now

Home in Indian Beach-Sapphire Shores

4.9 out of 5 average rating, 667 reviews

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

4.86 out of 5 average rating, 99 reviews

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

4.98 out of 5 average rating, 268 reviews

Guesthouse in Sarasota

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area offers. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

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Popular amenities for Longboat Key holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Longboat Key

4.57 out of 5 average rating, 7 reviews

Loft in Longboat Key

Inn on the Beach Beachfront Studio

TimothyRating, 5 stars1 month ago

I gave 5 stars for everything assuming I would be able to comment. I very rarely - if ever- write reviews. After paying there was some consternation on my part because I had not read all the "what's not included" info. Turns out- we did not miss being able to use the on premises bar and restaurants. This place was perfect for my wife and me. There are some good restaurants around - but not in "walking" distance - at least for an old fart like me. We did not have time to try all the local fare. I will not provide reviews of the restaurants here but I think our favorites were Lo'Key Grill, Drydock Waterfront Grill and Old Salty Dog. Pricing was increased for us because I bought trip insurance - not quite hurricane season when we visited but close enough to be cautious. The per night breakdown was a little more than I normally pay but we had a wonderful time, so no strong complaints.

Condo in Indian Beach-Sapphire Shores

5 out of 5 average rating, 9 reviews

Deluxe 2/2 Pool View, terraces, Top Floor

DoreenRating, 5 stars3 weeks ago

The Condo is very nice with beautiful view from the balcony, and equipped with all you need for your stay! We felt right at home! Clara was responsive and answered all of our questions. Thank you Clara!

5 out of 5 average rating, 7 reviews

Home in Cortez

Beach Retreat! Bikes, Paddleboards, Sauna & more!

MichelleRating, 5 stars11 months ago

Beautiful home and surrounding area, Pristine home in brand new condition. Expertly furnished, lots to do for teenagers, they loved the ice bath! Well stocked kitchen. The host was very responsive and helpful would definitely recommend this location and home. Happy vacationing.

4.97 out of 5 average rating, 181 reviews

Guesthouse in Bradenton

Sweet MERMAID #1

AdileneRating, 5 stars3 weeks ago

Really enjoyed my stay here! Close to the beach and was the perfect space for my partner and I for a mini weekend getaway.

4.98 out of 5 average rating, 50 reviews

Home in Bradenton

Cozy Cottage - close to Manatee River

BrianRating, 5 stars1 day ago

This cottage was cozy and beautiful. It had everything you needed and more. It was in a nice, quiet neighborhood & a close drive to the beach. We loved having access to the beach gear & the backyard had everything you could dream of. The hosts were friendly and helpful.

5 out of 5 average rating, 30 reviews

Condo in Madeira Beach

Oceanfront Loft w/ 2 Baths in Madeira Beach

KristinRating, 5 stars1 month ago

Absolutely beautiful location right on the beach. Walkable to shops and restaurants. Loved the balcony and view from upstairs.

5 out of 5 average rating, 12 reviews

Apartment in Lido Key

Family Beach Unit, Mid Week Special, Walk to Beach

DavidRating, 5 stars1 month ago

We had a great stay at Jarrod’s place! The apartment was super clean, well-equipped, and had everything we needed for a perfect beach getaway. The location is ideal—just a 10-minute walk or 2-minute drive to beautiful Lido Beach, and only about 4 minutes to nearby restaurants and shops. It was the perfect mix of convenience and comfort. Highly recommend for anyone looking to relax and enjoy the area!