House holiday rentals in Longboat Key

A custom pool is framed by elegant lounge chairs and tropical landscaping. Water features create gentle curves, while illuminated details enhance the space as the sunset casts a warm glow. A covered outdoor area is visible in the background, providing seating and entertainment options.

4.97 out of 5 average rating, 105 reviews

Fruit /Botanical Garden Estate 2 ml to downtown EV

Indulge at this Mediterranean estate, boasting lush botanical gardens and rare tropical fruit trees for your picking pleasure. Enjoy the custom pool, hot tub, sauna, cold plunge and the home gym. The expansive outdoor haven features a fully-equipped kitchen, fireplace, TV, and dining space. Enjoy leisurely games of pool, ping pong & shuffleboard, then retreat to the luxurious indoors with comfortable beds and a massive TV, all within the privacy of a walled-in estate. Your lavish escape awaits.

5.0 out of 5 average rating, 9 reviews

Carissa B | Beachside Retreat | Golf Cart | Pool

Carissa Loft B🏝️ A well-designed home offering comfortable spaces to relax, reconnect & experience all that AMI has to offer! Step inside to discover a private lower level retreat featuring a queen bed, sofa, TV and game table. Upstairs you'll find the fully stocked kitchen, inviting family room, 2-bedrooms & 2-full baths. The private outdoor oasis features a heated/cooled cocktail pool. 🚙Park the car & let the island adventures begin! The 6-person golf cart is complimentary with your stay!

4.97 out of 5 average rating, 113 reviews

The exterior of the beach house is depicted, showcasing a blue structure with a metal roof surrounded by tropical landscaping. A gravel driveway leads to the entrance, flanked by palm trees and vibrant foliage, emphasizing the inviting coastal atmosphere.

Home in Longboat Key

Beautiful Beach House

Beautiful, updated 1937 beach house. Original LongBeach cottage. Gated entrance to property. Three bedroom, two bath. Master bathroom has bathroom en suite. Hardwood floors throughout. Kitchen updated. Beautiful front and back porches to enjoy the sunshine. Private access to beach and Gulf of Mexico. Walking distance to shops and Tennis. Bedrooms include master with King, second bedroom with queen, third bedroom with two twins. Come join us in longboat key for sunshine, beaches,culture,tennis

4.95 out of 5 average rating, 199 reviews

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

4.95 out of 5 average rating, 63 reviews

A private heated pool is surrounded by a spacious patio with lounge chairs and an umbrella for shade. The modern two-story home features large glass doors that brighten the living spaces, and vibrant greenery enhances the outdoor area.

Home in Arlington Park

Private Heated Pool Retreat for Two Families

🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.

5.0 out of 5 average rating, 28 reviews

New! 4BR Villa + Crosswalk to Sand + Beach View!

Location ‼️ Location ‼️ 🌟🌴Welcome to Starfish Villa East, this Beachside home offers a private pool, putting green, & balconies with partial Gulf views. 🏖️Unwind across from the beach and fishing pier, and blocks from Bridge Street fun! ⛱️ Beach supplies included: wagon, 8 chairs, umbrella, cooler, and towels – everything you need for a perfect beach day 💃 Walking distance to Bridge Street, where you’ll find restaurants, shopping, bars, live music, attractions, ice cream, & mini g

4.98 out of 5 average rating, 128 reviews

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

A heated saltwater pool is surrounded by lush tropical vegetation, creating a serene atmosphere. Poolside seating is offered by several lounge chairs, alongside a shaded area with an umbrella. Sunlight reflects off the water's surface, enhancing the tranquil setting.

4.98 out of 5 average rating, 205 reviews

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

4.97 out of 5 average rating, 36 reviews

A clear view of a shared pool framed by palm trees, with sun loungers arranged around it. The pool area leads directly to the beach, visible in the background under a bright blue sky dotted with clouds. A sandy shoreline meets vibrant turquoise waters.

Home in Longboat Key

Beachfront Villa | Pool + Lanai | Hosts 6

Welcome to a slice of paradise on the coveted Longboat Key. Nestled beachfront, this two-bedroom villa offers barefoot luxury, breezy interiors, and a peaceful atmosphere that instantly slows the pace. Whether you’re here for a family getaway, a quiet reset, or just to listen to the waves with coffee in hand, this sun-drenched retreat delivers serenity in every square inch. **Part of the Turtle Crawl Inn ( Private Villa, Shared Pool )

4.88 out of 5 average rating, 17 reviews

Amazing location and location! One min. to Beach!

A charming 2BR/2BA beach house just a stone’s throw from the sparkling shores of Anna Maria Island. Walk to the beach, Publix, or Skinny’s Burger restaurant in minutes. Relax by the private pool or unwind in a lush tropical backyard filled with palms and coastal breezes. Bright, beachy interiors, a fully equipped kitchen, and cozy living spaces make this the perfect island escape for families, couples, or weekend getaways.

4.96 out of 5 average rating, 54 reviews

A serene sunset view is captured over the bay, with the sun sinking just above the horizon. Lush green grass stretches across the foreground, leading to calm waters. A private dock is visible, framed by coastal vegetation.

Home in Longboat Key

Right on the water with private boat slip

Beautifully furnished 2,500 sq ft 3bdrm/3bath (4 beds total) bayfront home with fabulous water views from nearly every room. Private slip & garage storage for your trailer. Bring your boat & leave it at the dock for your entire vacation. Gourmet kitchen. Spacious family room. Covered lanai. Private beach with chairs provided & community pool w/in a 3 minute walk. By far the premier home in the complex.

5.0 out of 5 average rating, 111 reviews

Bean Pt. Bungalow - Half duplex w/private pool

Welcome to Bean Pt. Bungalow! A charming 3/2 villa with a private saltwater pool in the heart of Anna Maria. You're only 0.2 miles from the nearest beach access and 0.2 miles from the Rod and Reel Pier. The home comes equipped with 6 beach chairs and cart. This boutique rental is the perfect place for your next getaway! Primary - King Bed Front bedroom - King bed Bunk room - 4 twin beds

Popular amenities for Longboat Key house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.

4.95 out of 5 average rating, 210 reviews

Private 30’ Pool &Boat Dock & Only Steps to Beach

The outdoor area features a spacious pool and a separate spa, surrounded by manicured gardens and palm trees. A covered lanai with steps leads to the upper level of the home, which includes expansive sliding glass doors inviting natural light into the interior.

4.97 out of 5 average rating, 38 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

Luxe

4.98 out of 5 average rating, 48 reviews

Just Pearly - 2 min walk to beach!

4.79 out of 5 average rating, 34 reviews

Playa Esmeralda Home! And add a golf cart!

An outdoor view showcases a private pool surrounded by lush landscaping and tropical palm trees. The distant beach features soft white sand meeting turquoise waters. A spacious deck, complete with loungers, offers a perfect relaxation spot under clear blue skies.

4.91 out of 5 average rating, 74 reviews

TOES IN THE SAND!

4.9 out of 5 average rating, 58 reviews

AMI Dock of the Bay - "On the Water" 1st Floor

4.93 out of 5 average rating, 27 reviews

Heated Pool, Hot Tub, Game Room, Steps to Beach!

4.96 out of 5 average rating, 26 reviews

A well-appointed outdoor area features an expansive heated pool with a vibrant blue hue, surrounded by stylish loungers and an outdoor dining space. Soft lighting highlights the sleek architecture of the home in the background, with lush greenery enhancing the atmosphere.

Home in Bradenton

Waterfront 5BR w/Pool, Spa, Boat Lift, Putting Grn

Weekly house rentals

A two-story beach house features a wooden staircase leading to a wrap-around balcony. Lush tropical landscaping surrounds the entrance, and several palm trees are visible. Large windows allow natural light to fill the home, enhancing the inviting facade.

4.98 out of 5 average rating, 41 reviews

Anna Maria Beach House

5.0 out of 5 average rating, 15 reviews

Home in Siesta Key

Steps to Siesta Key Beach! Sunset Balcony Views!

5.0 out of 5 average rating, 24 reviews

ShoreSideSuites Stunning Gulf Views|Steps to Beach

4.97 out of 5 average rating, 62 reviews

A serene backyard scene is highlighted by a sparkling pool, accompanied by lounge chairs and a hammock nestled among lush trees. The stylish bungalow features a spacious deck, creating an inviting atmosphere for outdoor relaxation. The sky is painted in calming hues as sunset approaches.

Home in Bradenton

10 min AMI | 15 min IMG | Heated Pool

4.88 out of 5 average rating, 24 reviews

Luxury Canal Home + Heated Pool/Spa, Sleeps 12

4.97 out of 5 average rating, 39 reviews

Private Heated Pool~Yacht Rental~BBQ~Near Water

5.0 out of 5 average rating, 11 reviews

NEW! w/ Pool - The Pearl Unit 2 on AMI

An aerial view showcases SunSalt Cottage surrounded by lush greenery and palms. The large private saltwater pool is visible, along with the tiki hut and outdoor seating area. The nearby beach and distant ocean can be seen beyond the charming homes of Anna Maria Island.

4.99 out of 5 average rating, 67 reviews

SunSalt Cottage~5 min to Beach, Shops & Food~Pool

Private house rentals

5.0 out of 5 average rating, 14 reviews

New! Pool + Rooftop+ 2 Min Walk to Beach & Bay!

5.0 out of 5 average rating, 15 reviews

Home in Arlington Park

5BR home w/ pool & hot tub

5.0 out of 5 average rating, 15 reviews

Dockside Dream:Luxury canal front home, dock, pool

4.98 out of 5 average rating, 83 reviews

Winter Haven Retreat – Steps to Bay & Ringling

4.95 out of 5 average rating, 59 reviews

A screened-in pool area features a clear blue pool surrounded by tropical greenery. Two lounge chairs with striped fabric are positioned nearby, alongside a shaded umbrella. The pool deck is spacious, inviting relaxation and leisure in a tranquil outdoor setting.

Home in Siesta Key

Siesta Key home 5 min from beach

Superhost

4.9 out of 5 average rating, 20 reviews

The Beach House 2 by Duncan Real Estate

4.94 out of 5 average rating, 33 reviews

Home in Cortez

Island Adjacent! 4 bed/3 bath home w/Pool & Tiki!