Vacation rentals with a pool in Longboat Key

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Longboat Key

  • Total vacation rentals

    Explore 790 vacation rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key vacation rentals start at €35 per night before taxes and fees

  • Verified guest reviews

    Over 8,540 verified reviews to help you choose

  • Family-friendly vacation rentals

    630 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    260 properties have a dedicated workspace

  • Wi-Fi availability

    760 of Longboat Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Longboat Key rentals

  • 4.8 Average rating

    Longboat Key stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Longboat Key

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.
Apartment in Longboat Key

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

4.96 out of 5 average rating, 125 reviews
Top guest favorite
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.
Home in Sarasota

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.

4.97 out of 5 average rating, 103 reviews
Top guest favorite
Condo in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

4.96 out of 5 average rating, 111 reviews
Top guest favorite
Apartment in Longboat Key

Cozy private beach condo

Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enjoy breakfast, lunch or dinner with the beautiful view of the Golf of Mexico right from your lanai. This lovely condo has 2 bedrooms 2 bath with small office and full equipped kitchen. The condo is located in a second floor accessible by stair and just a short walk to the complex 600 feet of white sand beach front, heated pool and bbq area. Minimum of 2 week rental available

5.0 out of 5 average rating, 30 reviews
Guest favorite
A sandy pathway leading to a beach is framed by lush dune vegetation. The scene captures a vibrant sunset over calm waters, with soft clouds reflecting warm hues. Natural light creates an inviting atmosphere, highlighting the serene transition from land to sea.
Condo in Longboat Key

Gulfront Views! BEACHFRONT BARGAIN HUNT NOMINATED

THIS UNIT WAS NOMINATED TO BE FEATURED ON BEACHFRONT BARGAIN HUNT! Unit #102 Features: Full-size kitchen and Gulf-front views Bedding: 1 Queen Murphy Bed and a Sleeper Sofa Savor warm Gulf breezes while resting lavishly in this Gulf-front condo complex. Located directly on the beach, this resort features beautiful Gulf-front views. You are only steps from the white-sand beaches, placid turquoise waters and beautiful sunsets that will have you daydreaming about your next beach vacation.

4.8 out of 5 average rating, 143 reviews
Top guest favorite
Apartment in Longboat Key

Beach Bliss!

This sublime oceanfront studio condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the ground floor, overlooking the heated pool and ocean, this dreamy studio is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

5.0 out of 5 average rating, 122 reviews
Top guest favorite
A bright living area is showcased, featuring a light-colored sectional sofa and an accent chair. A large flat-screen TV is mounted on a stylish entertainment unit. Decorative elements include soft textiles and natural light streaming in from multiple windows, enhancing the open-concept layout.
Apartment in Longboat Key

Waterfront 2BR 2BA | Pool - 10 min walk to Beach

A spacious first-floor 2-bedroom, 2-bathroom condo with direct pool access and stunning bayfront views. Located just a 10-minute walk to the beach, this beautifully appointed retreat offers the perfect blend of comfort, relaxation, and convenience. Enjoy a private patio overlooking the bay, a fully equipped kitchen, and a bright, open living space. With resort-style amenities, including a pool, hot tub, and tennis courts, it’s an ideal escape for couples, families, and remote workers.

5.0 out of 5 average rating, 14 reviews
Top guest favorite
A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.
Condo in Longboat Key

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

4.9 out of 5 average rating, 238 reviews
Top guest favorite
Apartment in Longboat Key

New Modern on Beach- Walk out 5 steps to Sand

Newly renovated modern first floor condo literally five steps away from the sand walking outside from the lanai. One bedroom /One bath King bed in Primary Queen sleeper sofa in living room Key code entrance Free parking Heated Swimming pool on site Free Beach loungers on the beach Paid laundry machines on site Mid Island next to everything WiFi, cable, free parking Usually 7 night minimum Bring your toothbrush and bathing suite and prepare to unwind and relax!!!!

5.0 out of 5 average rating, 36 reviews
Top guest favorite
Condo in Longboat Key

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 5% among Airbnb’s homes.

4.98 out of 5 average rating, 109 reviews
Guest favorite
Condo in Longboat Key

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

4.88 out of 5 average rating, 139 reviews
Top guest favorite
An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.
Condo in Longboat Key

The Beach Condo #107 Beachfront Full View

Unit #107 has private beach access. Only a few steps to the beach will full gulf view. This end condo unit is quiet, ground floor . It is a small studio: new queen murphy bed and queen sofa bed. No separate bedroom. Limited initial limited supply of products/soaps/towels. Common use W/D across from unit. This is a small studio at 330 sq ft. It has been recently remodeled. Grounds, unit, pool recently renovated due to hurricanes.

4.87 out of 5 average rating, 209 reviews

Popular amenities for Longboat Key rentals with a pool

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Avg. price€237€293€318€278€233€233€195€183€171€183€210€232
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