Holiday rentals with a pool in Sarasota Springs

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Top-rated rentals with a pool in Sarasota Springs

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

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Guest favourite

Guest suite in Sarasota

4.89 out of 5 average rating, 110 reviews

Downtown privacy, beaches and nightlife all around

For the couple (or individual) who wants a fabulous private home and is in a centrally-located space in downtown Sarasota. Where the beaches meet the nightlife (Legacy Trail is 5 short blocks away, pickle ball 3 and Robarts Arena 2), this separate In-Law Suite has its own entrance, private patio and lots of space (1,000 sq. feet). 2 bikes and beach items for use are: chairs, umbrellas, noodles and coolers. The washer/dryer is attached, high-speed internet/cable; there is a gas grill, 2 tvs

19–26 Jul

₹10,655 per night

Guest favourite

Guest suite in Sarasota

4.94 out of 5 average rating, 286 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *COVID Cleaning. SELF CHECK IN. Non shared Pool. Bungalow w/private entrance & patio. Designers Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Key Beach, shops, dining, & 5mins/Downtown Sarasota core. Walk to local markets, dining, movies & shopping. New King bed. New 50" TV. Off street parking. No Smoking/Vaping! Wet Bar, No kitchen, lite meals only! No hotels in my exclusive area! Live like a local!

13–20 Oct

₹15,638 per night

Guest favourite

Flat in Sarasota

4.96 out of 5 average rating, 207 reviews

Private 2 Bedroom Suite with Kitchenette

A lovely private suite, attached to our home, consisting of 2 bedrooms, bath, and kitchenette/dining area. Features a private entrance and use of our family pool, lanai & sauna. Located close to I75, and minutes away from Nathan Benderson Park, and the Mall at University Town Center where you'll find many shopping & eating options. You will also be only 12 miles from the beautiful white sand beach of Siesta Key with all of the activities it affords. Located in a family friendly neighborhood.

15–20 Jun

₹11,337 per night

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

3–10 Nov

₹53,626 per night

Guest favourite

Home in Sarasota

4.97 out of 5 average rating, 116 reviews

Private Pool Oasis 3BR/2BA near Siesta Key Beach

Modern Private House with a pool near Siesta Key will be your home away from home! This renovated house has plenty of privacy, space and a lot of sunlight. Luxurious sleeping arrangements will guarantee a relaxing sleep. A quiet neighborhood with a lot of privacy and convenient proximity to all main attractions. A very spacious outdoor space at the pool will be your favorite spot for family dinners and entertainment. This house will be your favorite spot to relax and enjoy your vacation.

3–10 Jan

₹30,975 per night

Guest favourite

Guest house in Sarasota

5.0 out of 5 average rating, 102 reviews

Magical Guesthouse 1 mi from SRQ airport

Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

16–23 Nov

₹11,566 per night

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 123 reviews

Cool Pool Wood House

Our home is filled with many amenities including pool towels, beach chairs, coolers, fully stocked kitchen, and more. The decor is a nice blend of modern farmhouse and mid century. The heated pool is screened in complete with lounge chairs and dining table for those beautiful evening dinners in Fla. Located on a very quiet dead end street within walking distance to the unique village of Pinecraft where you can enjoy restaurants, coffee shop, homemade pizza shop and more!

16–23 Jan

₹26,346 per night

Guest favourite

Guest house in Sarasota

4.89 out of 5 average rating, 168 reviews

Supercute Beach Themed Retreat Free Parking Wi-FI

Come and enjoy our newly remodeled 400 square foot laid back beached themed guest house. Located just 1.5 miles away from Sarasota/ Bradenton airport, and less than 10 miles away from our world famous beaches. Whether you are a single person in search of a long term stay or a family looking for a short vacation, we have the place for you. Our guest area is attached to our main residence and has a private entrance. Enjoy our shared swimming pool and outside patio areas.

7–14 Jul

₹11,143 per night

Guest favourite

Home in Sarasota

4.93 out of 5 average rating, 140 reviews

Sarasota Sandpiper: 4 Bed/3 bath + Pool

Your Ideal Getaway: All-Inclusive Comfort and Convenience Discover the perfect retreat that's close to everything you desire in a vacation. Whether you're seeking the beach, family-friendly activities, nightlife, mini golf or championship golf courses, you'll find it all at your doorstep. It's a place where you can unwind and savor life's simple pleasures. Embrace the great outdoors with an outdoor space that's perfect for relaxation and enjoyment.

19–26 Sep

₹20,646 per night

Guest favourite

Guest house in Sarasota

4.99 out of 5 average rating, 131 reviews

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!

13–20 Jul

₹12,234 per night

Guest favourite

Home in Sarasota

4.91 out of 5 average rating, 105 reviews

Charming Sarasota Home with Pool!

Charming 3/2 home with a pool! very safe neighborhood, 8.9 miles to Siesta Beach and 5.5 miles to Lido Beach. 15 minute walk to The quaint little village of Pinecraft and Der Dutchman Restaurant and more restaurants and shops. Very clean, private back yard, heated pool, coffee station... really everything you need for a relaxing and enjoyable stay in Sarasota.

6–13 Apr

₹25,686 per night

Guest favourite

Home in Sarasota

4.95 out of 5 average rating, 181 reviews

2bed/2bath with POOL house, close by SIESTA KEY!!!

By customers requirements from April 1st will be HEATED POOL! Living room has a sectional with pull out full size bed. 1st. bedroom king size bed, 2nd. bedroom queen size bed. House great for families, located within 10-15 mins of siesta key beach #1 beach in US. 10 minutes from Sarasota Downtown. NOTE: We allow ONLY dogs till 30lb. For Extra 150$ fee.

17–24 Sep

₹18,212 per night