Vacation rentals with a pool in Ridge Wood Heights

4.91 out of 5 average rating, 372 reviews

Bungalow in Sarasota

Pool & fenced-in yard in downtown edge bungalow

MESSAGE ME FOR DAYS YOU DONT C. This 2 bed-2 bath house is a homey Florida bungalow with wood floors & natural light in a quiet neighborhood on the downtown core edge. Spacious and private fenced-in backyard with pool, covered grill and eating area. Minutes away from the Legacy Trail, the Bay Park, Payne Park, dining, live music, bars, theatres, comedy, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

A swing chair hangs from the ceiling in a cozy living space, complemented by a dark sectional sofa and a round coffee table. A decorative rug adds warmth to the wooden floor, while a wall-mounted television and a piece of artwork provide visual interest.

4.81 out of 5 average rating, 170 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

12 min. from Siesta Key Beach!! Perfect cozy vacation home in quiet, friendly neighborhood. Central to lots of shopping/restaurants. 1-king, 1-queen, bunk beds w/ 1-full & 1-twin. Dog & cat friendly w/ large private fenced yard, & 1-men's & 1-women's bike. Air hockey table w/ board games & pool toys. Fully loaded kitchen & W/D. Spacious living w/ large sectional, swing chair, & all bedrooms come w/ TVs & free Netflix & Hulu. Looking forward to hosting you! Message me anytime w/ questions.

The outdoor area features a uniquely shaped heated saltwater pool with clear blue water. Surrounding the pool are loungers placed on a bright, white deck, complemented by tropical plants and palm trees that enhance the tranquil environment.

4.98 out of 5 average rating, 114 reviews

Tropical Oasis Heated Pool Hot Tub Near Siesta Key

Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!

A bright pink flamingo float adorns the clear, inviting waters of the heated pool. Two white umbrellas provide shade for the striped lounge chairs nearby. Flower pots add a touch of greenery to the poolside area, which is enclosed by a white privacy fence.

4.94 out of 5 average rating, 116 reviews

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Enjoy Sarasota in one of the most desirable neighborhoods by Siesta Key! Truly an elite location, take Siesta Dr down to the well-documented #1 beach in the US in around 10 mins. Flourishing Downtown Sarasota is just 5 mins away. The house features a brand new heated pool, fenced in back yard with pavers, open concept living, beautiful kitchen with everything you need, upgraded bathrooms and plenty of space for a big family. We look forward to hosting you and yours!

A serene community pool is surrounded by a fence and complemented by lounge chairs positioned nearby. The pool's clear blue water reflects the sunlight, while the yellow exterior of the building provides a warm backdrop. Windows with awnings complete the inviting atmosphere of the area.

4.94 out of 5 average rating, 160 reviews

Villa Maria: Minutes to Siesta Key!

2 BDRM/2 BTHRM condo very close to Siesta Key (3 min. drive or 20 min. walk). Totally UPDATED! Quality furnishings, super clean, ideal location. Have it all: Spacious condo in a peaceful setting. Just a few minutes drive over the south bridge to Siesta Key. Walking distance to great restaurants and shops on and off the key. Everything is within easy access by walking, car, bike, or free beach shuttle service. Come enjoy everything Sarasota has to offer.

4.99 out of 5 average rating, 144 reviews

A light blue bedroom features a spacious bed with a floral-patterned blanket and a ceiling fan overhead. Double glass doors provide a view of the pool area outside. Storage options include a white dresser and closet, while a small table and chair are positioned nearby.

Guesthouse in Sarasota

Maggie's Hideaway

This adorable little bungalow is hidden away in one of Downtown Sarasota's oldest historical neighborhoods and only a couple miles from Sarasota Bay and surrounding beaches. Beautiful Lido Beach is only five miles west, Siesta Key is seven miles southwest, with Benderson Park being only seven miles east. Fabulous shopping and world class dining is plentiful in this downtown community. There is plenty to see and do in Sarasota - Come see us!

The outdoor area features a heated pool surrounded by a serene landscape of palm trees and decorative stones. An adjacent BBQ grill offers outdoor cooking options, while comfortable seating is available nearby. The patio area is partially shaded by a pergola, providing a relaxing space.

4.96 out of 5 average rating, 223 reviews

The Oasis-Heated Private Pool Hot Tub-5mi to beach

"The Oasis" is a renovated beach cottage with heated private pool & hot tub in the heart of Sarasota. It's 5 miles to the #1 beach in the USA: Siesta Key Beach. The cottage offers 2 bedroom & 2 bathrooms, and a bonus room that can be used to sleep 6 comfortably. The one-of-a-kind fully private, fully enclosed backyard includes heated pool, hot tub, BBQ grill, outdoor dining table & fire pit for families & snowbirds to enjoy Florida living!

A spacious screened lanai features a circular wooden table surrounded by two wooden chairs with patterned cushions. Potted plants and decorative items are placed on the table. Beyond the railing, palm trees and the vibrant blue of the Gulf coast are visible.

4.91 out of 5 average rating, 122 reviews

Siesta Key Beach Front Condo

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

The living room features a spacious layout with a comfortable gray sofa and rocker recliner. A dining area with a table for six is present, alongside large glass doors that provide ample natural light and a view of the surrounding greenery. A flat screen TV is visible.

4.97 out of 5 average rating, 130 reviews

Siesta Key Condo. Checkout our great rates!

Our beautiful Siesta Key condo is located a short stroll from the famous Siesta Key beach with its beautiful quartz sand and amazing sunsets. The Midnight Cove II condominium complex has private beach access with outstanding amenities and is very family friendly, come and enjoy the natural beauty this complex and all Siesta Key has to offer.

Apartment in Gillespie Park

A private entrance is framed by a sleek plant and modern features. The entrance door is flanked by a wall light and a smooth concrete pathway, complemented by potted plants that enhance the outdoor space.

4.97 out of 5 average rating, 180 reviews

Gillespie On The Park, Walk to Downtown

Contemporary Studio apartment with balcony above garage. Studio is half block from Gillespie Park with its public walking/jogging/biking paths, tennis courts, basketball court, and retention pond. Within walking distance to downtown and Rosemary District: restaurants, shops, movie theaters, cultural events, Whole Food Market, Starbucks etc.

4.86 out of 5 average rating, 345 reviews

A bright pool area is enclosed by a screened structure, featuring a sparkling pool with a curved edge. A detached two-story apartment stands adjacent, accessible by stairs. Lush greenery and potted plants enhance the serene atmosphere, creating a residential retreat.

Apartment in Laurel Park

Sarasota Downtown close to Lido Beach

Beautiful Studio Apartment in the heart of Downtown Sarasota, Marina Jack Harbour, St. Armands Circle & Lido Key Beach. Queen size bed, Direct TV, WiFi Internet, washer/dryer. Detached apartment next to a private home and pool.

4.99 out of 5 average rating, 119 reviews

Guesthouse in Sarasota

Sarasota Pool House

Great location.Minutes to Siesta key beach (5.5 Mile.)Walking distance to Westfield Siesta Key Mall. Downtown Sarasota(3.5 mile)Airport (7.5 mile).Lido Beach (6.7 mile) Sarasota Memorial Hospital (2.3 mile ).

Popular amenities for Ridge Wood Heights rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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 out of 5 average rating, 84 reviews

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

5 out of 5 average rating, 4 reviews

Gulf Gate Dream 2bd 2ba Htd Pool Beaches Shopping

A spacious living room is presented with neutral-toned sofas adorned with colorful cushions. A coffee table with decorative items is centered between the seating, while light enters through large windows framed by soft blue curtains. A decorative plant adds a touch of greenery.

4.97 out of 5 average rating, 36 reviews

Great Rates! Sunny Sarasota Villa! W/ 2 bicycles!

The modern kitchen features a large island with a marble countertop, topped with an arrangement of fresh fruits and drinks. A light fixture adds a soft glow above the island, while a cozy seating area with a dark sofa and brick wall can be seen in the background.

4.87 out of 5 average rating, 113 reviews

Sarasota Getaway “Have some fun under the sun.”

4.85 out of 5 average rating, 102 reviews

Roselawn St | Private Pool, Fire Pit + Patio!

A private courtyard featuring a heated pool is surrounded by lush tropical landscaping. Comfortable lounge chairs are positioned beside the pool, and a small fountain adds a soothing element. A cozy seating area is visible near the entrance to the adjoining building.

4.94 out of 5 average rating, 129 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

The exterior of a newly renovated home is shown, featuring a light-colored brick facade and a modern garage door. A well-maintained driveway leads to the entrance, which is accentuated by a bright orange door. Landscaping includes gravel beds and low-maintenance plants amidst partial cloud cover.

4.89 out of 5 average rating, 90 reviews

Gorgeous renovation with pool, minutes from beach

A private backyard oasis is highlighted by a heated pool and a hot tub, surrounded by lush tropical landscaping. A shaded area with an umbrella and seating for outdoor dining is visible beside the pool, creating a serene environment for relaxation.

4.97 out of 5 average rating, 118 reviews

Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees

Condo rentals with a pool

A serene lanai view features a dining table with chairs overlooking the community pool. Lush palm trees frame the scene, while sunlight reflects off the water's surface. A doorway is visible, leading to the interior of the condo.

4.96 out of 5 average rating, 214 reviews

Gateway to Siesta Key - 1/2 Mile to the Beach

An aerial view captures the expansive white sand beach and turquoise waters, lined with beachgoers. The surrounding buildings and amenities are visible, including pools and recreational areas, creating a vibrant coastal atmosphere. Cloud patterns add depth to the bright blue sky above.

4.93 out of 5 average rating, 122 reviews

Beautiful White Sand Siesta Key Beach

A living area features a comfortable green sofa complemented by a lamp casting a warm glow. A white wicker chair adds a coastal touch, positioned beside a small white table. Light wooden floors extend across the space, with soft wall art and a wall-mounted TV enhancing the environment.

4.83 out of 5 average rating, 260 reviews

Cozy 1BR Beach Condo on Siesta Key!

An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.

4.92 out of 5 average rating, 148 reviews

Sea Shell Ocean View On Beach Walk Everywhere Pool

A vibrant exterior showcases the entrance to Villa Maria, framed by palm trees and a charming fountain. The entrance features a set of red stairs leading to a welcoming sign, adding a decorative touch to the well-maintained surroundings.

4.91 out of 5 average rating, 151 reviews

Gateway Siesta Key Beach

4.97 out of 5 average rating, 126 reviews

A screened lanai offers a peaceful retreat with a view of the pond and trees reflecting on the water. Comfortable seating is provided, accompanied by a small table. Natural light flows in, enhancing the serene atmosphere of the space.

Condo in Bradenton

A&A's Paradise near IMG & Anna Maria beaches

4.9 out of 5 average rating, 206 reviews

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

A three-story condominium building is shown, featuring a combination of palm trees and lush green landscaping at the forefront. Balconies are visible on each level, with a red-tiled roof adding a distinct character to the architecture.

4.95 out of 5 average rating, 110 reviews

Seaside on Siesta Key Beach

Other vacation rentals with a pool

Apartment in Southside Village

A bright pink flamingo float rests partially submerged in the clear water of a swimming pool. Sunlight reflects off the surface of the water, enhancing the pool's inviting atmosphere. Surrounding lounge chairs are positioned along the poolside, emphasizing a leisure-friendly environment.

4.97 out of 5 average rating, 39 reviews

Siesta Key 2 miles! Pool, Steps to Dining, +Bikes!

4.97 out of 5 average rating, 77 reviews

A heated pool is surrounded by lush greenery, with clear blue water inviting relaxation. Sunlight glimmers on the surface, and a cozy pool area is visible alongside a white two-story building. The space features a kayak resting against the pool's edge.

Apartment in Sarasota

Beechwood Suites A

A spacious living area features a gray sofa and armchair, accented by bright orange and yellow decorative elements. A large window brings in natural light, showcasing a view of greenery. A vibrant area rug adds color, while a media console and coffee table complete the setting.

4.86 out of 5 average rating, 73 reviews

The Perfect Shiny Oasis

4.97 out of 5 average rating, 33 reviews

Charming Poolhouse · 1BR · Close to Siesta

A serene outdoor space features a refreshing pool with clear water surrounded by a sunlit patio. Lush green grass borders the pool area, while tropical plants add a natural touch. A neutral-toned wall serves as a backdrop, enhancing the peaceful atmosphere.

5 out of 5 average rating, 14 reviews

House minutes to Siesta

4.95 out of 5 average rating, 19 reviews

Lanai w/ Pool Views • Minutes to Siesta Key

4.9 out of 5 average rating, 52 reviews

Updated condo minutes to Siesta Key Beach