Vacation rentals with a pool in Fruitville

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Top-rated rentals with a pool in Fruitville

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

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Guest favorite

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

Jun 26 – Jul 3

$105 per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 285 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!

Feb 20 – 27

$160 per night

Guest favorite

Bungalow in Sarasota

4.92 out of 5 average rating, 310 reviews

Pool & fenced-in yard in downtown edge bungalow

This 2 bed-2 bath house is a homey Florida bungalow with cypress wood floors and lots of natural light, located in a quiet neighbourhood on the downtown core edge. Enjoy a spacious and fenced in backyard with pool, covered grill and eating area. The home is minutes away from the Legacy Trail, the new Bay Park, Payne Park, dining, live music, bars, theatres, opera house, performance venues, comedy club, antiquing, kayak launches, tennis and basketball courts, farmer's market, shopping and more.

Nov 5 – 12

$142 per night

Guest favorite

Apartment 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.

Jun 15 – 20

$115 per night

Guest favorite

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.

Apr 19 – 26

$299 per night

Guest favorite

Home in Sarasota

4.81 out of 5 average rating, 107 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.

Sep 26 – Oct 3

$143 per night

Guest favorite

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!

Aug 8 – 15

$225 per night

Guest favorite

Guesthouse in Sarasota

4.89 out of 5 average rating, 167 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.

Sep 30 – Oct 7

$89 per night

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 130 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!

Aug 25 – Sep 1

$116 per night

Guest favorite

Guesthouse in Sarasota

4.88 out of 5 average rating, 96 reviews

Guest house w/heated salt water pool and Game Room

This special place is close to everything, 10 min to Beautiful Siesta Key and 15 to Longboat key. Brand new UTC mall is a 10 min drive. Be the first to enjoy our new renovations and upgrades!! Private free parking on property. Heated salt water pool and game room! Covered BBQ area with seating, bluetooth speakers, TV and Free wifi. Host can also decorate room for special occasions... birthdays, anniversary, valentines, etc...

Feb 25 – Mar 4

$89 per night

Guest favorite

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.

Sep 18 – 25

$262 per night

Guest favorite

Condo in Siesta Key

4.87 out of 5 average rating, 210 reviews

Siesta Key Beach Community!

Two bedroom, one bath fully furnished condo. Fantastic location on Siesta Key. local bus goes to nearby Siesta Village & #1 beach in the US. Heated pool, tennis court and clubhouse. BBQ, picnic area and fishing pier located on the bay side. one king bed and one full. Siesta beach is less than a mile with free parking and crescent beach is a 10 minute walk.

Jun 21 – 28

$130 per night