Beach house holiday rentals in Longboat Key

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Top-rated beach house rentals in Longboat Key

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Guest favourite

Home in Seminole

4.89 out of 5 average rating, 103 reviews

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!

Top guest favourite

Home in Indian Rocks Beach

5 out of 5 average rating, 26 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.

Top guest favourite

Home in Indian Rocks Beach

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

Guest favourite

Home in Indian Rocks Beach

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

Top guest favourite

Home in Siesta Key

4.99 out of 5 average rating, 81 reviews

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!

Top guest favourite

Home in Indian Rocks Beach

5 out of 5 average rating, 47 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

Guest favourite

Home in Sarasota

4.88 out of 5 average rating, 158 reviews

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

Superhost

Home in Indian Rocks Beach

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

Home in Siesta Key

4.91 out of 5 average rating, 23 reviews

Siesta Key Hideway -3 bedroom canal pool home

Take a moment to enjoy the quiet side of Siesta Key. This home sits on a tree canopied street and offers a rare and serene location along with 3 large bedrooms and open plan living and dining. Cook in the gorgeous kitchen while looking out over the mangrove lined canal. Walk through the neighborhood , spend time on the patio or in the pool and take in the calm beauty that this home offers. All of this lies a short distance from the beach, Siesta Village, Sarasota and surrounding areas.

Top guest favourite

Home in Indian Rocks Beach

5 out of 5 average rating, 48 reviews

Walk to Beach! Waterfront Lux Retreat w/Kayaks

Experience the serene beauty of a waterfront Indian Rocks Beach Home. Wake up to breathtaking views of the water, right from your window. Enjoy the luxury of kayaking or fishing off your private boat dock. Spend evenings gathered around the fire pit or showcase your culinary skills with our grill. Our home is impeccably designed to ensure you relax in style. Just a 7-minute walk and you'll find yourself on the pristine white sands of Indian Rocks Beach. Kayaks and boat lift available.

Top guest favourite

Home in Holmes Beach

4.97 out of 5 average rating, 32 reviews

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!

Superhost

Home in Anna Maria

4.9 out of 5 average rating, 20 reviews

Beach N Bay 206 by Duncan Real Estate

Welcome to Beach N Bay 206! Pool COOLING for hot summer days! A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Maria, one of Coastal Living Magazine's Top 10 Happiest Seaside Towns! Located right in the middle of all that happiness, Beach N Bay is the island vacation cottage duplex that's so tropical and fun, you'll swear you can hear steel drums!