Vacation rentals with a pool in Longboat Key

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.

4.96 out of 5 average rating, 125 reviews

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).

4.97 out of 5 average rating, 103 reviews

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.

4.96 out of 5 average rating, 111 reviews

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!

5.0 out of 5 average rating, 30 reviews

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

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.

4.8 out of 5 average rating, 143 reviews

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.

5.0 out of 5 average rating, 122 reviews

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...!

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.

5.0 out of 5 average rating, 14 reviews

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.

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.

4.9 out of 5 average rating, 238 reviews

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.

5.0 out of 5 average rating, 36 reviews

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!!!!

4.98 out of 5 average rating, 109 reviews

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.

4.88 out of 5 average rating, 139 reviews

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.

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.

4.87 out of 5 average rating, 209 reviews

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.

Popular amenities for Longboat Key rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 202 reviews

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

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

4.98 out of 5 average rating, 128 reviews

Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

4.89 out of 5 average rating, 159 reviews

Home in Bradenton

Ocean View of AMI | Hot Tub | IMG | 6 TVs | 2 King

4.98 out of 5 average rating, 103 reviews

A well-maintained front yard features lush green grass and a large agave plant. The house, showcasing a contemporary design, is flanked by palm trees. A driveway leads to a two-car garage, with additional landscaped areas adding to the outdoor appeal.

Home in Cortez

Dockside Dreams - Pool, Spa & Waterfront Dock

4.82 out of 5 average rating, 104 reviews

An outdoor dining area is set with a glass table and six blue chairs, shaded by a blue umbrella. In the background, a swimming pool with surrounding tropical plants invites relaxation, while a spa is visible nearby, offering a serene ambiance.

Home in Holmes Beach

Private pool, only two blocks .3 miles from beach!

4.94 out of 5 average rating, 109 reviews

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 Sarasota

Retreat by the Bay-Heated Saltwater Pool

4.81 out of 5 average rating, 117 reviews

Home in Bradenton Beach

AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks

4.96 out of 5 average rating, 107 reviews

A private pool is surrounded by tropical landscaping, featuring a clear blue water surface that reflects soft lighting. Several lounge chairs are positioned nearby, providing relaxation space under the palm trees. The serene area is perfect for unwinding after a day at the beach.

Home in Anna Maria

Beach House w/Private Pool & Spa

Condo rentals with a pool

4.88 out of 5 average rating, 112 reviews

Condo in Holmes Beach

#terraceLIFE | 2 Blocks to Beach | Heated Pool

4.85 out of 5 average rating, 102 reviews

A serene view from a balcony is presented, showcasing calm waters and lush greenery along the shoreline. Two wicker chairs and a round table are positioned on the balcony, enhancing the inviting outdoor space. The sky is clear, reflecting soft natural light on the water.

Condo in Bradenton Beach

Charming 2BD/2BR with Big Water Views on the beach

4.99 out of 5 average rating, 159 reviews

A modern kitchen area features pale blue walls and a round dining table set for four. Stainless steel appliances, including a microwave and oven, are visible. A decorative light fixture made of translucent discs hangs above the table, adding a coastal touch to the space.

Condo in Holmes Beach

Short Stroll to the Surf! ~ Make Memories on AMI

4.92 out of 5 average rating, 170 reviews

Condo in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

4.92 out of 5 average rating, 165 reviews

Condo in Siesta Key

Gulf Views | Walkable | Spacious

4.97 out of 5 average rating, 137 reviews

A serene pool area is bordered by palm trees, reflecting the gentle hues of a sunset. Lounge chairs are arranged around the pool, and a shaded cabana is visible in the background. The tranquil water mirrors the evening sky, enhancing a peaceful atmosphere.

Condo in Siesta Key

Heated Pools & Spa · Private Beach + Bay Views

4.92 out of 5 average rating, 125 reviews

A two-story yellow condo is highlighted against a clear blue sky. Palm trees line the pathway leading to a fenced pool area. The entrance features a covered balcony with white railings, offering a welcoming view of the surrounding tropical landscape.

Condo in Bradenton Beach

Beachy Chic! 1st Floor Condo-Pool-Close to Beach

4.85 out of 5 average rating, 110 reviews

The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.

Condo in Siesta Key

Comfy Siesta Key Condo

Other vacation rentals with a pool

Casa particular in Longboat Key

Seaside Cottage Retreat Steps Away From the Beach

5.0 out of 5 average rating, 3 reviews

4.97 out of 5 average rating, 29 reviews

Just renovated, beach view from balcony Unit 203

An enclosed terrace features a dining table surrounded by white chairs, offering expansive views of Sarasota Bay. Palm trees sway gently outside, while boats are visible in the distance. Natural light floods the space through large glass windows, creating a serene atmosphere.

4.97 out of 5 average rating, 72 reviews

Secluded Bayside Gem with beautiful bay views

5.0 out of 5 average rating, 6 reviews

Second Floor Studio- Amazing Gulf Front Views

5.0 out of 5 average rating, 35 reviews

Sunset and Beach view unit 402

Aerial view of a wide beach features soft white sand and gentle waves lapping at the shore. The water displays a gradient of turquoise to deep blue, with scattered footprints in the sand. The horizon meets a clear sky, enhancing the open coastal atmosphere.

4.94 out of 5 average rating, 67 reviews

Turtle walk - Next to 7 top eats-Beach Easy walk

A private balcony offers views of the tranquil Gulf of Mexico, with lush greenery bordering the shoreline. A table with a vase of flowers is visible, inviting relaxation. The swimming pool can be seen below, along with chaise lounge chairs arranged for sunbathers.

4.77 out of 5 average rating, 92 reviews

Amazing beachfront View & balcony on Long Boat Key