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

Jul 19 – 26

G$26,144 GYD per night

Guest favorite

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!

Oct 13 – 20

G$38,369 GYD 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

G$27,788 GYD 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.

Jan 3 – 10

G$75,951 GYD per night

Guest favorite

Condo in Sarasota

5.0 out of 5 average rating, 26 reviews

Water view condominium in a beautiful community

You will love the beautiful views this condo has to offer. Combo dining room/living room opens up to a fully screened lanai with tranquil water view on the golf course and the community pool/deck area only steps away. The Meadows is located close to downtown Sarasota, minutes from University Town Center Mall, short drive distance to the beautiful Golf coast beaches. With 1650 acres, The Meadows is home to an abundance of canopied oaks, over 85 lakes and waterways, and 14 miles of trails.

Jan 3 – 10

G$26,762 GYD per night

Guest favorite

Condo in Bradenton

4.94 out of 5 average rating, 108 reviews

Newly remodeled cozy 2 bed/2.5 bath townhome

Fully renovated 2 bedroom/2.5 bathroom townhome nestled in a quiet, gated community in Bradenton between I-75 and some of the best beaches in the country. My townhome features 2 bedrooms (queen size) with en suite bathrooms. Beds are queen size. Amenities in the neighborhood include: large heated pool, tennis and basketball courts, playground, volleyball area, sport field, and designated parking spot steps away from the front door. Non-numbered guest parking is also available.

Nov 26 – Dec 3

G$36,273 GYD 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!

Jan 16 – 23

G$64,631 GYD per night

Guest favorite

Guesthouse 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.

Jul 7 – 14

G$27,347 GYD per night

Guest favorite

Home in Sarasota

5.0 out of 5 average rating, 16 reviews

Beautiful Nautical Home Near Doctors Hospital

Beautifully furnished 2 Bedroom/2 Bath close to Doctor's Hospital and 3 prestigious SRQ Country Clubs. The large fenced in backyard and screened in Florida room are perfect for 2 couples visiting or snowbirds wanting a little extra space. Comes with a fully equipped kitchen, luxury linens, washer/dryer, and ping pong table. We are close to the beach and provide beach chairs and an umbrella. We have two beach cruisers for you to enjoy during your stay.

May 30 – Jun 6

G$30,882 GYD per night

Guest favorite

Guesthouse 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!

Aug 13 – 20

G$27,721 GYD 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...

Sep 11 – 18

G$21,549 GYD 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.

Apr 6 – 13

G$63,625 GYD per night