Beach house vacation rentals in Longboat Key

4.89 out of 5 average rating, 104 reviews

An aerial view showcases a vibrant outdoor area featuring a heated and cooled pool, colorful mats arranged neatly on the grass, and a cheerful Lite Brite wall. Lounge seating and a movie area with large bean bags are visible by the poolside, inviting relaxation and fun.

Home in Seminole

Fun Beach Escape: Pool Bar, Mini-Golf, Pong, Games

Welcome to our Lite Brite Beach Escape! No matter your age or interest, we have something for everyone! Heated & cooled pool ⭐ Mini-golf ⭐Lite Brite wall⭐Outdoor movie theater⭐ Pong⭐Bikes ⭐Beach gear ⭐Games ⭐Slide & playhouse We invite you to explore your creative and fun side while experiencing the beauty and wonders of Florida on the Gulf Coast! We provide a long list of basic amenities so your stay is seamless and stress-free. Just pack your personal belongings and we have the rest covered!

4.88 out of 5 average rating, 159 reviews

The exterior of a well-maintained condominium is displayed, featuring a two-car garage and neatly trimmed hedges. Palm trees and lush landscaping frame the entrance, while a clear blue sky enhances the tropical feel of the setting.

Home in Sarasota

5 minutes to private Siesta Key Beach + 2 pools

Escape to this luxurious 1st-floor condo on Siesta Key, just 5 minutes from the award-winning Siesta Key Beach. Enjoy private access to its soft, white sand and turquoise waters. Perfect for families, the condo offers two heated pools, lighted tennis and pickleball courts, a fishing pier, gym, and sauna for endless fun and relaxation. Nestled in a tropical setting, it’s the ideal spot for your beach vacation, staycation, or a peaceful getaway. Everything you need for an unforgettable experience!

5 out of 5 average rating, 27 reviews

Beach access! Private Pool! Whole house 2 Kitchens

This PRIVATE oasis has beach access off the pool patio, just a 2 minute walk down the shell lined Beach Trail! Boasting full remodel in 2025 with two kitchens & PRIVATE POOL, outdoor shower & multiple patio areas! Located on the beach side of Gulf Blvd, we are a fan favorite among returning guests who enjoy many restaurants within walking distance! Four parking spaces included at no additional charge. Dock your boat just 3 blocks away at Harborside Marina! Golf cart rental also available nearby.

A spacious outdoor area features a heated above-ground pool, surrounded by a gravel surface and plants for privacy. A hot tub is positioned nearby, along with a BBQ grill and patio seating. A lounge chair with a beach towel lies centered in the area.

4.98 out of 5 average rating, 180 reviews

Luxe BeachHouseA Heated Pool, 2 min walk to Beach

Welcome to your home away from home.Sand,sun and ocean breeze are waiting for you.Our modern Beach House is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built three story house with nice and private backyard,heated pool,hot tub and beautiful rooftop.We have everything that you need for bigger groups of families to relax on your Beach vacation.Our Beach House is in a quite neighborhood and walking distance from restaurants,bars and stores. BTR#209

A light-filled dining area is presented with a simple white table surrounded by four matching chairs. Large glass doors offer views of the waterfront, while sunlight reflects off the gentle water outside.

4.96 out of 5 average rating, 51 reviews

Breakfast wDolphins! Private waterfront POOL

Nice vintage 1950's cottage in a quality beach residential neighborhood. See dolphins & seasonal manatees & nature watch from the dock. Rent kayaks & explore or book a poolside massage, an experience like no other at this peaceful paradise! 10ish minute walk to beach access. All new furniture Jan. '25! There are very few of these waterfront cottages left! Please scroll down to full House Rules tab & extend the tab for more info on booking, guest, & pet requirements /house care. Thanks! BTR1925

4.99 out of 5 average rating, 82 reviews

An airy dining area features a glass table supported by a unique wooden base, surrounded by four woven chairs. Natural light floods the open space, highlighting the modern kitchen with white cabinetry and high-end finishes, while a large pendant light adds a stylish touch.

Home in Siesta Key

Relax in a Private Tropical Retreat on Siesta Key!

Your dream vacation awaits with a renovated, spacious, and private single-level house. It's a perfect getaway for a relaxing vacation! Enjoy all the comforts of home while being just a short walk away from restaurants, bars, and Siesta Key's beautiful white sand beaches. Nestled on a quiet tree-lined street and tropical gardens, this retreat offers tranquility and serenity. The community boasts a large heated pool and intercoastal waterway pier, ideal for afternoon fishing or sunset beverages!

Views of the waterfront highlight the tranquil setting, with a private heated swimming pool surrounded by lush greenery. Palm trees frame the scene, and colorful boats are visible in the distance against a clear blue sky.

5 out of 5 average rating, 49 reviews

Waterfront Indian Rocks Beach Gem

Premier location in the popular beaches of Tampa Bay/ Clearwater area. -Five minutes walk to the popular Indian Rocks Beach -Amazing water views and lots of natural light -Private heated Swimming Pool & Spa -Kayak for two and 2 stand boards - 2 Bikes -Gaming Room with PS5 & Nintendo switch, 2 car driving sets -Gym - Billiard, Ping Pong table, Fossball and accessories -TV in every room-Disney, Prime, Netflix, Max, Hulu -Projector at the pool -All beach needs -Fishing rods - Grill - Al Amenities

A sunlit sunroom opens to a private deck overlooking the water. Bright blue outdoor chairs are positioned on the deck. Textured walls are complemented by a lamp and potted plant, creating a coastal vibe, while a sign labeled 'BEACH' is displayed above the doorway.

5 out of 5 average rating, 10 reviews

Playa Vista Villa

This home is a haven less than two blocks from the white sand of Indian Rocks Beach and RIGHT on the intercoastal. Cozy and beautifully appointed, once you're inside, you can tune out the rest of the world, and bird and dolphin-watch from the sunroom or private deck. Or, open the front door and walk to your choice of six restaurants, CVS, a brew pub, CrossFit, convenience store, surf shops - all in under 5 minutes. All the comforts of home, and then some, in a compact and brand-new package!

Superhost

The outdoor pool, surrounded by palm trees, reflects the clear blue sky. Comfortable loungers are placed nearby, offering ample space for relaxation. The glistening water leads to views of the waterfront, enhancing the serene atmosphere of the outdoor environment.

4.83 out of 5 average rating, 341 reviews

Stunning views! Spot dolphins from the pool!

BTR#2114 This home has it ALL including incredible open water sunsets! Every detail has been carefully thought out and updated. This is a VERY upscale, coastal, single story waterfront home. A complete waterfront remodel w/ dock & pool that looks and feels like a new home w/ stunning water views from your own back patio! The water glistens and sparkles from 3 pm thru sunset and after, the sky is set on fire for 40 minutes. White sandy beach is only few blocks away! Amazing home inside & out!

Superhost

The exterior features a vibrant turquoise facade, complemented by a screened lanai. Surrounding the space are tropical landscaping and a rock garden. Blue chairs invite relaxation beneath the shade of trees, enhancing the outdoor experience in a serene atmosphere.

Home in Anna Maria

4.55 out of 5 average rating, 33 reviews

Minnow 2 by Duncan Real Estate

Easy Island living at Minnow 2 will want you to stay longer! This property is half of a ground level duplex. This beautiful and tastefully decorated two-bedroom, one bathroom beach cottage has polished terrazzo throughout. It sleeps up to four people in total. If you have more people in your party consider renting Minnow 1 which is the other half of the duplex. HIGHLIGHTS 624 sq ft. 222 sq ft. of deck space Screened Lanai 0.1 miles from bay access 0.2 miles from beach access

4.97 out of 5 average rating, 34 reviews

A tropical backyard features a heated saltwater pool surrounded by palm trees and vibrant landscaping. Lounge chairs are arranged beside the pool, and an outdoor covered seating area with colorful chairs provides a relaxing retreat. A light-colored home stands in the background.

Home in Holmes Beach

Loggerhead - AMI Oasis w/ Private Pool + Golf Cart

Loggerhead is back and ready to welcome you! ️ Escape to the tranquility of Anna Maria Island in this charming 2-bedroom, 2-bathroom home nestled on a peaceful, secluded street. Relax in your private tropical backyard featuring a heated saltwater pool. You'll never need to worry about parking just steps from the beach, about a 4 minute walk. We provide everything for your getaway including beach essentials and a 6-person street-legal golf cart. Your perfect family paradise awaits!