House holiday rentals in Longboat Key

An aerial view captures a heated private pool surrounded by tropical landscaping. Deck chairs and a lounge chair provide seating options, and stone pathways lead to the pool. The pool curves gracefully, inviting relaxation in a serene outdoor setting.

4.98 out of 5 average rating, 114 reviews

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

LocationValueView

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

LocationFamilyDecor

5.0 out of 5 average rating, 135 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream A purpose-built luxury family vacation home designed by parents for unforgettable stays. Enjoy swing dining chairs, a glowing neon moss wall, backyard putt-putt, and a free heated saltwater pool (Nov 21–Apr 1st). 15 minutes to Siesta & Lido Key Beaches. ✔ Private heated saltwater pool ✔ Backyard mini golf & outdoor games ✔ Luxury covered lanai w/ high ceilings ✔ Super kid-friendly (toys, Pack ’n Plays) ✔ Jura Espresso Machine ✔ 65” Frame TV w/ YouTube TV

LocationValueIndoor spaces

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

LocationFamilyPool

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.

ValueLocationCleanliness

A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.

4.97 out of 5 average rating, 111 reviews

Salty Harbor AMI pool retreat near the Beach

Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

FamilyValueOutdoor spaces

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.

FamilyLocationLaundry

4.9 out of 5 average rating, 20 reviews

Home in Longboat Key

Dog friendly LBK home with deeded access to beach!

**Calendar not always up to date. Please message me for specific dates. Newly renovated 3/2. Location, location, location. Walk or ride bikes to some of the top restaurants on LBK. Perfect for a small family or two couples. Beautiful outdoor screened in porch with grill, couches, dining room set and and ping ping table, outdoor living at its best. Tenants also get to enjoy Cedar’s Racquet Club membership with pool, tennis, pickle ball, full gym and bikes.

LocationFamilyGetting around

A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.

5.0 out of 5 average rating, 110 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

LocationFamilyKitchen

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.

LocationFamilyOutdoor spaces

5.0 out of 5 average rating, 109 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

FamilyValueWalkability

4.98 out of 5 average rating, 130 reviews

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

ValueFamilySleep quality

Popular amenities for Longboat Key house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Superhost

An outdoor space showcases a heated saltwater pool with a calm blue hue, surrounded by comfortable lounge chairs. The area is framed by lush greenery and fencing, enhancing privacy. The backdrop features a gently lit sky at dusk, complementing the home's modern design.

4.95 out of 5 average rating, 110 reviews

Retreat by the Bay-Heated Saltwater Pool

ValueLocationAmenities

Luxe

4.98 out of 5 average rating, 48 reviews

Just Pearly - 2 min walk to beach!

LocationFamilyLayout

5.0 out of 5 average rating, 8 reviews

The Lookout by Beach Boutique Rentals

LocationLayoutBeach

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

LocationFamilyAir conditioning

5.0 out of 5 average rating, 9 reviews

Carissa B | Beachside Retreat | Golf Cart | Pool

FamilyLocationNearby

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!

LocationFamilyAccess

A charming beach house is surrounded by lush palm trees and tropical landscaping. The exterior features a light blue color, and balconies are visible on the upper level. A paved pathway leads to the front entrance, creating an inviting approach.

4.95 out of 5 average rating, 64 reviews

Anna Maria - 3 Bd 2 Bth-Heated Pool-Walk to Beach

LocationValueCheck-in

4.79 out of 5 average rating, 34 reviews

Playa Esmeralda Home! And add a golf cart!

LocationValueCheck-in

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

FamilyLocationComfort

5.0 out of 5 average rating, 9 reviews

Home in Bayshore Gardens

King Beds | Game Room | Putt Putt | Pool |

FamilyOutdoor spacesBeach

4.93 out of 5 average rating, 27 reviews

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

LocationFamilyPets

4.9 out of 5 average rating, 58 reviews

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

FamilyLocationLayout

5.0 out of 5 average rating, 20 reviews

New Listing! 4BR + Beach View + Heated pool!

LocationFamilyBackyard

4.96 out of 5 average rating, 78 reviews

Renovated 2bed /2 bath North End, beach 2 min walk

ValueFamilyBackyard

5.0 out of 5 average rating, 10 reviews

Sun Coast Oasis-Heated Pool-Pool Table-Arcade

FamilyLocationBeach

5.0 out of 5 average rating, 36 reviews

New! Heated Pool • Shopping • Pine Ave • Beaches!

LocationFamilyKitchen

Private house rentals

4.96 out of 5 average rating, 50 reviews

Home in Bradenton

The Florida Rooms

LocationFamilyIndoor spaces

4.94 out of 5 average rating, 33 reviews

Home in Cortez

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

LocationFamilyCleanliness

A private heated pool is surrounded by lush tropical landscaping and features a stone border. A patio area with outdoor furniture is positioned nearby, while palm trees gently sway in the breeze. The bright blue sky enhances the serene atmosphere of the space.

4.86 out of 5 average rating, 65 reviews

Cozy Cottage - POOL HOME! 3/3

FamilyLocationComfort

5.0 out of 5 average rating, 19 reviews

Casa Cay by Duncan Real Estate

LocationFamilyGetting around

5.0 out of 5 average rating, 24 reviews

Pergola Oasis | Walk to Beach + Outdoor Living

FamilyLocationSleep quality

A cozy living room area features a light-colored entertainment center with a large flat screen TV. Comfortable seating is arranged around a wooden coffee table. Natural light enters through nearby windows, enhancing the calming atmosphere.

4.94 out of 5 average rating, 32 reviews

Cayman Cay #201 - Beach & Pool

LocationFamilyCondition

4.95 out of 5 average rating, 21 reviews

Home in Lido Key

Beautiful Home Steps to Gulf w/ Pool, Spa & Views

FamilyLocationTV

A stunning sunset is captured over the ocean, with warm hues of orange and gold reflected on the water. Silhouetted palm fronds are visible in the foreground, and the roof of a nearby building is partially seen, adding depth to the coastal scene.