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House vacation rentals in Longboat Key

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Top-rated house rentals in Longboat Key

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A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.

Home in Holmes Beach

4.95 out of 5 average rating, 110 reviews

Breezy Harbor AMI pool retreat near the Beach

Stunning Fall 2024 renovation done! Charming Breezy Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immediately feel stress melting away. You'll love grilling in the lush yard and a 6-min walk to the beach or the AMI trolley stop. A supermarket is a couple of streets over. The home is perfect for families, couples, 1-50Lb pet, and working remotely. Ample Parking for 2 vehicles and toys. *Ask us for shorter stays and always discuss your pets with us*

The home's exterior is softly illuminated by warm lights, highlighting the paved driveway and tropical landscaping. Tall palm trees and lush greenery surround the entrance, creating a serene atmosphere. The modern roof adds a contemporary touch, enhancing the inviting appearance of the property.

Home in Longboat Key

4.85 out of 5 average rating, 131 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

A curved swimming pool is set against a backdrop of lush tropical foliage and palm trees, with water views extending to a nearby dock. Brightly colored pots with plants are placed around the pool area, enhancing the serene outdoor setting.

Home in Sarasota

4.96 out of 5 average rating, 71 reviews

True Island Living House/beach/water views

Charming Bayfront Home in heart of Siesta Key. 3 bdrm/3.5 bath, full water views, spectacular sun rises, private, gas heated pool, boat dock/ lift, outdoor sitting area /lush tropical landscape. Open floor plan, contemporary decor, gas fireplace, hardwood floors throughout, updated kitchen, stainless steel appliances, granite counters and a full walk-in pantry. 2 Master Suites upstairs and one guest bdrm on main floor. Washer and dryer inside, 3 TV’s. Outdoor shower. Fishing. Parking for 2 cars.

Top guest favorite

Home in Clearwater

4.98 out of 5 average rating, 173 reviews

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's w/ Sling & Roku. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

An elegant outdoor space features a heated pool surrounded by stylish stone pavers and tropical landscaping. Large covered porches provide shaded seating areas with colorful furniture, while palm trees enhance the inviting atmosphere of the home's exterior.

Home in Bradenton

4.95 out of 5 average rating, 148 reviews

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

Lounge chairs with decorative blue cushions are arranged on a patio, overlooking a serene body of water. A lush green lawn extends in front of the water, and the sky is tinted with soft hues of orange and pink from the setting sun.

Home in Sarasota

4.97 out of 5 average rating, 30 reviews

Right on the bay! Heated pool! King bed

Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. You will have whole house except two rooms which will be locked and no one will be there. One bedroom with a king size bed and sleeping sofa in the family room (if more than two guests coming). Full size kitchen, two family rooms, pool and gorgeous view on the salty bay for nature lovers.

A private heated pool is enclosed by a screened lanai, surrounded by lush tropical plants. Soft purple lights create a relaxed ambiance. Comfortable seating and dining areas are positioned nearby, inviting leisurely moments by the water.

Home in Indian Beach-Sapphire Shores

4.97 out of 5 average rating, 154 reviews

ROYS PLACE private, tropical, romantic paradise.

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR 2022, 2023, 2024. An exceptional vacation is a frame for an exceptional life. Offered for you, a romantic boutique home. Sarasota Chic decor, quality furnishings, lush tropical landscaping. Only property in urban Sarasota with your own private (EXCLUSIVE to you, NOT shared) CLOTHING OPTIONAL heated pool for tropical fun. One block walk to beautiful sunsets over Sarasota Bay. All tropical serenity yet close to everything.

A screened-in porch features a green wooden floor and white railing, providing an inviting space to relax. Coastal wicker chairs are arranged for comfort, with light filtering through lush greenery, creating a serene atmosphere. Decorative plants enhance the warmth of the space.

Home in Longboat Key

4.89 out of 5 average rating, 9 reviews

Beautiful Island Beach House

Beautiful Island Beach House with pool/hot tub and private beach access on Longboat Key. The large light-filled spacious home is close to everything that you want for a fun, yet relaxing beach vacation: restaurants, bars, shopping, nature walks, and sandy white private beaches. Due to island restrictions, a 28-day stay is the shortest rental period allowed. Please note that this property is not available for young children given the surrounding water. Ages over 6 are welcome with supervision.

Top guest favorite

A bright and airy living room features a large, blue sectional couch adorned with decorative pillows. A flat-screen TV is mounted on a stone accent wall, while natural light filters in through sheer white curtains. A wooden coffee table displays a small decorative tray.

Home in Clearwater

4.94 out of 5 average rating, 115 reviews

Best Location in Clw! Near Beach & Saltwater Pool!

PRIME LOCATION NEAR BEACH! Welcome to our newly renovated vacation home in beautiful Clearwater, FL. Located in the heart of downtown Clearwater within walking distance to several restaurants and shops and just a few mins drive to Clearwater Beach. This coastal styled home comes with a heated pool (at no extra charge), putting green, and a fun little game room for kids! The entire home is yours to enjoy and comes fully stocked with everything you need for a relaxing beach getaway vacation.

Top guest favorite

A spacious living area features blue leather sofas arranged around a plush blue pouf. Natural light enters through large windows, illuminating the terracotta tiled floor. A wooden staircase leads to an upper level, while a surfboard decorates the wall, adding a coastal touch to the space.

Home in Anna Maria

4.93 out of 5 average rating, 14 reviews

Bayfront Beach access with Heated Pool!

Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views of Tampa Bay & the iconic Skyway Bridge. The backyard oasis features a refreshing saltwater pool & fully fenced backyard, complete w/artificial turf & outdoor shower. Just steps away, you'll find full access to a stunning white sandy beach & the crystal-clear waters of Tampa Bay! Conveniences have been carefully considered, creating the most ideal vacation destination!

A bright living area is shown, featuring a comfortable gray sofa with patterned throw pillows. A light-colored coffee table sits on a textured area rug. Large glass doors open to a lush backyard, which can be seen through sheer white curtains, allowing natural light to fill the space.

Home in Sarasota

4.95 out of 5 average rating, 110 reviews

Rita Retreat - Beautiful 2/2 with private pool

Welcome to your dream vacation home! This charming rental offers a private pool and a lush green area for relaxation and fun. Situated just 4.6 miles away from the stunning Siesta Key beach, you'll have easy access to sun-kissed sands and sparkling waters. Seafood lovers will be delighted to find the renowned Phillippi Creek Oyster Bar nearby, offering some of the best seafood in town. Embrace the Florida lifestyle and make cherished memories in this wonderful retreat!

Top guest favorite

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.

Home in Bradenton Beach

4.97 out of 5 average rating, 174 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.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Longboat Key house rentals

Free parking on premises

Air conditioning

House rentals with a pool

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.

Home in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 93 reviews

Retreat by the Bay-Heated Saltwater Pool

Top guest favorite

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

Home in Holmes Beach

5 out of 5 average rating, 45 reviews

Labor Day SALE act now Beachview~Pool~Free trolley

Top guest favorite

A spacious outdoor area features a large checkers and chess board on a checkered surface, surrounded by vibrant green artificial grass. A pool area is visible in the background, with a privacy fence and sunlit space for leisure activities.

Home in Pinellas Park

4.98 out of 5 average rating, 134 reviews

Insta Worthy Retreat - Heated pool-putt putt | Bar

An inviting outdoor space features a private in-ground saltwater pool, surrounded by green grass and lounge chairs. Tropical landscaping provides a serene backdrop, with various plants and trees enhancing the atmosphere. Two umbrellas and a shaded seating area facilitate relaxation and outdoor enjoyment.

Home in Sarasota

5 out of 5 average rating, 3 reviews

Artsy 3BR/2BA Pool Home Arlington Park

An outdoor space is enclosed with a screened canopy, featuring a private pool and a fire pit surrounded by ample lounge chairs. Tropical palm trees frame the area, while soft lighting enhances the inviting atmosphere. A covered seating area is visible in the background.

Home in Sarasota

5 out of 5 average rating, 9 reviews

Legacy's Palm of Paradise | Pool+ Putt Putt Course

Top guest favorite

A warm outdoor space features a heated pool surrounded by tropical landscaping. Comfortable black lounge chairs are positioned nearby, providing a relaxing area for guests. Soft lighting illuminates the space, creating a serene atmosphere in the evening.

Home in Holmes Beach

5 out of 5 average rating, 49 reviews

Perfect Hideaway- Post Storms Better Than Ever!

Top guest favorite

A spacious outdoor area is presented, featuring stylish wicker seating around a wooden coffee table. Lush, green turf is visible, along with palm trees and a vibrant blue sky. A cornhole setup is positioned on the lawn, providing a fun area for outdoor activities.

Home in Bradenton

4.95 out of 5 average rating, 149 reviews

Spa+Pool+Yard Games+2 Master+Upscale Area+Spacious

Top guest favorite

Home in Holmes Beach

4.98 out of 5 average rating, 48 reviews

Unwind Sunshine: steps to locals' favorite beach

Weekly house rentals

A spacious screened patio surrounds a heated pool, featuring a bright blue star-shaped float and a yellow flotation device. Lush greenery is visible outside the enclosure, and the clear sky allows sunshine to illuminate the outdoor space.

Home in Sarasota

4.98 out of 5 average rating, 80 reviews

FREE Heated XL Pool|Baby Gear|Beach|UTC|SRQ

Top guest favorite

An expansive outdoor space features a heated pool and an 8x8 spa, surrounded by a stone patio. Lounge chairs and a patio dining set are arranged invitingly. The sky is painted with soft hues of orange and pink as twilight descends.

Home in Sarasota

5 out of 5 average rating, 45 reviews

Sarasota Memories For a Lifetime

Top guest favorite

A bright kitchen is showcased, featuring modern cabinetry and appliances. A small dining area with two wooden stools is positioned next to a white countertop. Natural light fills the space through a nearby door and window, creating an open atmosphere.

Home in Bradenton

4.99 out of 5 average rating, 96 reviews

Tranquility on the bay.

A spacious garage is visible, featuring paddleboards, a ping pong table, and various outdoor equipment. Two beach cruiser bikes with light blue frames and brown accents are positioned in front, adding a beachy touch to the inviting environment.

4.93 out of 5 average rating, 15 reviews

Beach Retreat! Bikes, Paddleboards, Sauna & more!

Top guest favorite

A screened outdoor space features a swimming pool with clear blue water. Comfortable seating arrangements, including dark wicker chairs with soft cushions, are positioned next to the pool. A dining set is visible in the background, surrounded by lush greenery.

5 out of 5 average rating, 38 reviews

Heated saltwater CAGED pool ! NEW ! CLEAN !

Top guest favorite

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.

Home in Bradenton Beach

5 out of 5 average rating, 71 reviews

Location! Beach Access + Restaurants + Trolley!

Top guest favorite

The open-concept living area features a modern dining table set with intricate lace placemats. A pink sofa and white chairs provide ample seating, complemented by a stylish chandelier overhead. Bright natural light fills the space, highlighting decorative plants and framed artwork.

Home in Anna Maria

5 out of 5 average rating, 79 reviews

Wanderlust Villa

The charming two-story house features a welcoming front porch with decorative railings, surrounded by lush tropical landscaping. Light yellow siding and white accents enhance the exterior, while a paved driveway leads to a garage underneath. The blue sky above adds a bright touch to the scene.

Home in Anna Maria

5 out of 5 average rating, 9 reviews

September Golf Cart Special

Private house rentals

Top guest favorite

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.

Home in Sarasota

5 out of 5 average rating, 66 reviews

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

An inviting poolside area is seen with submerged lounge chairs and a clear blue pool, illuminated in soft pink tones. Surrounding seating includes a shaded umbrella and chairs, with scenic water views beyond. A tree provides gentle shade, enhancing the tranquil outdoor setting.

Home in Apollo Beach

5 out of 5 average rating, 15 reviews

Waterfront Retreat in Apollo Beach –Relax & Unwind

Top guest favorite

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

Home in Palm Harbor

4.95 out of 5 average rating, 76 reviews

Private pool, Golf Cart, Completely Renovated!

Top guest favorite

A spacious pool area features a clear blue pool with a spa, surrounded by a tiled deck. Comfortable seating areas are provided, including lounge chairs and a fire pit. Lush greenery and tall trees create a serene atmosphere, enhancing the outdoor experience.

Home in Sarasota

5 out of 5 average rating, 83 reviews

The Blessing House- Htd Pool/Spa, Close to Beaches

An aerial view of a charming ground-level vacation home is presented, featuring a light-blue exterior and a metallic roof. Surrounded by lush tropical landscaping, a clear pool reflects the sunlight, and a patio area with lounge chairs is visible in the background.

Home in Anna Maria

5 out of 5 average rating, 13 reviews

Sea Shack - 2bd/2ba POOL Home

Top guest favorite

A private pool area is surrounded by lush greenery and palm trees. The curved pool features clear blue water, complemented by lounge chairs and a shaded seating area. A second-story balcony offers scenic views, while a barbecue grill is positioned nearby for outdoor dining.

Home in Bradenton Beach

5 out of 5 average rating, 27 reviews

Sunset View

Top guest favorite

An inviting two-story blue house is surrounded by lush greenery and palm trees, providing a tropical feel. A paved driveway leads to two garage doors, while a welcoming front porch with white railings offers a glimpse of the home's charm.

Home in Bradenton Beach

5 out of 5 average rating, 11 reviews

Casa Bonita

Top guest favorite

A two-story yellow house is set amidst lush tropical landscaping. A gravel driveway leads to the elevated front entrance, which features a spacious porch with white railings. Palm trees and vibrant foliage surround the property, creating a serene atmosphere.

Home in Anna Maria

5 out of 5 average rating, 33 reviews

'Walk on the Beach" heated pool North End AMI

Quick stats about house rentals in Longboat Key

Total rentals
220 properties
Nightly prices starting at
G$6,272 GYD before taxes and fees
Total number of reviews
4.3K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
140 properties have a pool

Destinations to explore