Vacation rentals with a pool in Ridge Wood Heights

An expansive backyard features a private heated pool, surrounded by lounge seating and a well-maintained putting green. Softly glowing twilight casts a warm hue over the space, framed by lush greenery and a serene atmosphere.

5 out of 5 average rating, 102 reviews

Living The Dream: Heated Pool + Mini Golf +Swings

BNB Breeze Presents: Living The Dream! From the swings at the dining room table and the neon sign, to the moss wall and the private putt-putt course, Living the Dream is fully loaded and is the ultimate luxury vacation home! Located just 15 minutes away from BOTH Lido Key and Siesta Key Beach, this incredible stay includes: ✔ Backyard Putt-Putt Course ✔ Private Heated Saltwater Pool w/ Lounge Chairs ✔ Covered Patio w/ String Lights ✔ Jura Espresso Machine ✔ 65" Frame TV w/ Youtube TV Included!

An outdoor dining area is featured with a round stone patio. A table with six black chairs is positioned underneath a large red umbrella, providing shade. Lush greenery and a fenced area create a serene backdrop for outdoor meals.

5 out of 5 average rating, 22 reviews

Poolside Paradise on Quiet Cul-de-Sac Near Beach

Your family-fun pool and beach vacation starts here! Your group will love the quiet cul de sac, screen-enclosed pool, fully equipped kitchen, and 1-level living with no stairs to climb. Grab the supplied beach accessories and head to beautiful Siesta Key beach, voted the country’s No. 1 beach, 4.7 miles away. Enjoy outdoor living that includes splashing in the pool, grilling and dining on the patio or relax in the heated pool or beachside. You’ll be close to dozens of Sarasota attractions, too!

A screened-in heated pool area is enveloped by lush greenery and vibrant garden elements. A soothing rock waterfall is visible, alongside white lounge chairs and a shaded seating area. Sunshine filters through the enclosed space, highlighting the inviting blue water of the pool.

4.88 out of 5 average rating, 16 reviews

Coastal Calm - 3BD/2BA Heated Pool Near Beaches

Just a short drive to Siesta Key Beach, Downtown Sarasota, and top local attractions! Explore Marie Selby Gardens, rent a boat to go fishing, visit UTC for shopping and dining experiences, see animals at Jungle Gardens, indulge in Amish cooking at Pinecraft Amish Village, and more! Enjoy time together at local family parks, great restaurants, and vibrant churches like South Shore Community Church. We've thoughtfully equipped our home to make your stay as fun and comfortable as possible!

5 out of 5 average rating, 20 reviews

Sun & Swim Villa W/ Fence + Pool by Siesta Key!

Modern home w/ private heated pool, Smart TVs, & Giant Jenga! Perfect for families as it comfortably sleeps 16 people and is located in a peaceful neighborhood. 4 Miles away from the Siesta. -Fully Fenced -2 Walk In Showers! -Unlimited High-Speed internet. -Keurig Coffee Maker w/ K Cups -Crock Pot Slow Cooker -3 Rooms with King Beds -Room with 2 Bunk Beds (Twin Top, Full Bottom) -Living room features a double sleeper sofa plus 2 roll away cots available -Parking for up to 6 cars

A fenced backyard showcases a heated pool surrounded by landscaped areas. Lounge chairs are positioned beside the pool, inviting relaxation. Sunlight reflects off the water, while a screened lanai provides a shaded space for enjoyment.

5 out of 5 average rating, 15 reviews

Renovated charmer w/ heated pool

Your family will be close to everything when you stay at this centrally-located place - 2 miles from Siesta Key Beach and 3 miles from downtown Sarasota. The house is fully renovated and the property enclosed with 8ft fence ensuring complete privacy. The spacious landscaped backyard with screened lanai and heated pool provides for a perfectly enjoyable and relaxing time. The 2 bedroom, 2 bathroom home is elegantly yet practically appointed for a comfortable stay for 4 people.

A screened outdoor area features a heated pool accompanied by a spacious seating arrangement. A dining table with chairs sits shaded under an umbrella, while lounge chairs are positioned nearby. Lush greenery provides a natural backdrop, enhancing the inviting space.

4.96 out of 5 average rating, 146 reviews

Beautifully Remodeled Home with Pool Near Siesta

It’s all about Siesta! Newly remodeled, 2 bedrooms, 2 baths, heated pool home is located in the Gulf Gate Estate neighborhood. 2,5 miles from the famous Siesta Key Beach. Great split plan bedrooms and bathrooms. High-speed Wi-FI. Located less than a mile from Publix Grocery, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Walking distance from the nearest convenient/gas station-7Eleven (5min). Parking for up to 3 cars maximum. Must be at least 25 years old.

A sparkling pool is surrounded by a spacious patio, featuring lounge chairs and a vibrant red umbrella. Lush tropical landscaping creates a serene retreat, providing an inviting space for relaxation and leisure under a clear blue sky dotted with fluffy white clouds.

4.96 out of 5 average rating, 124 reviews

Mid-Century Oasis with Pool in Arlington Park 1

A perfect blend of Sarasota’s architectural heritage and contemporary elegance right in the heart of Arlington Park. This bright, newly renovated 2 bed/2 bath & pull out sofa in a mid-century gem offers a serene escape, providing a refreshing interplay of historical charm and modern luxury. Enjoy the separate sunroom/office for those working from home, or use as an extra sleeping space with comfy pull out sofa. Take a break with a quick dip in the sparkling pool.

A modern house with a light-colored exterior is set against a clear blue sky. A private saltwater pool reflects sunlight, surrounded by sleek loungers. Lush greenery borders the space, and outdoor seating is visible on a covered patio, creating an inviting area for relaxation.

5 out of 5 average rating, 16 reviews

New modern home, minutes from Siesta Key beach!

Beautiful, luxury brand new construction modern energy efficient home located 10 minutes from Siesta Key Beach in a quiet and residential neighborhood that is close to shopping, dining and Sarasota Downtown. This large, two-story house with a luxury roof terrace and patio will not disappoint you. The highlights for this amazing design is the balcony on the second floor, luxury opened terrace ideal for entertaining or enjoying a moment of silence to read a book.

A serene pool area is surrounded by lush greenery and wooden fencing. Aquamarine water reflects sunlight, while a few poolside lounge chairs in turquoise invite relaxation. Potted plants add a touch of color, and a floating pool accessory rests on the surface.

4.93 out of 5 average rating, 107 reviews

5Stars Tiki, Heated Pool, Close to Beaches and ALL

Beautiful home with amazing pool and landscape, 15 minutes from Siesta Key Beach, 25 minutes from Lido Key Beach and Venice Beach. Close to grocery stores, parks, biking trails, shopping and restaurants. Enjoy the pool, entertain your family in our tiki bar, meditate in our amazing backyard or rest in our tastefully decorated bedrooms. Two pets under 30 pounds are allowed. Our pet fee is $150/dog. Please enter your pet when you complete the reservation.

A refreshing scene features a sparkling heated pool surrounded by lush greenery. A table displays vibrant lemons and limes alongside sparkling water with lemon slices. A blue frog statue adds a whimsical touch to the serene pool area.

4.96 out of 5 average rating, 211 reviews

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

"The Oasis" is a newly 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, with 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 and snowbirds to enjoy Florida living!

4.98 out of 5 average rating, 142 reviews

Beautiful 3 Bd, 2 bth Pool Home Near Siesta Key!

Stay in your own very private oasis in this 3 BR, 2 BA home with a heated pool. Well-appointed and newly updated kitchen. Large living room with 14-ft. ceilings & huge flatscreen TV's in 3 rooms. Shopping center is a 10 minute walk with fine dining, a grocery store, ice scream, salon and more. All of this and just a few miles to Siesta Key beach and downtown! The reviews say it all! :-)