Vacation rentals with a pool in South Sarasota

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Top-rated rentals with a pool in South Sarasota

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

R2,280 ZAR 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

R3,482 ZAR 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

R2,524 ZAR per night

Guest favorite

Condo in Sarasota

4.96 out of 5 average rating, 120 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

**No Kids allowed** Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, There is a pull-out large kitchen table. Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

Dec 15 – 22

R2,887 ZAR per night

Guest favorite

Home in Sarasota

4.95 out of 5 average rating, 410 reviews

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Jul 22 – 29

R6,525 ZAR per night

Guest favorite

Home in Sarasota

4.97 out of 5 average rating, 206 reviews

Your private retreat near Siesta Key Beach.

Your Private Retreat! Nestled at the end of a quiet dead-end street. This distinguished rental property guarantees a relaxing Florida vacation for everyone! Completely remodeled with Coastal-Modern Decor. Beautifully appointed, 3 bedroom, 2 bath, heated pool home is located in the Gulf Gate Estate neighborhood. A short drive (less than 2 miles) to the white coastal sands of Siesta Key Beach, Gulf Gate shopping mall, grocery store, restaurants, cafes, pubs. Must be at least 25 years old.

Oct 11 – 18

R6,115 ZAR per night

Guest favorite

Apartment in Sarasota

4.94 out of 5 average rating, 133 reviews

Super Clean! 2/2 condo Walk to SKey!

2 bedroom condo very close to Siesta Key (3 min. drive or 20 min. walk). All updated (including all new flooring and bathroom tiles since these photos)! Even nicer than before! 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.

Sep 21 – 28

R2,803 ZAR 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

R1,930 ZAR per night

Guest favorite

Condo in Sarasota

4.89 out of 5 average rating, 127 reviews

Gateway to Siesta Key 1/2 mile to the Beach!

Super comfy and newly updated 2 bedroom/2 bathroom fully-equipped condo that sleeps 4 - only 1/2 mile from the Gulf of Mexico! Located in a small and quiet complex with very convenient access to the beach as well as all of Sarasota's shopping and dining (without beach traffic). Our condo is exceptionally clean, well-kept and has all the comforts of home on your tropical getaway. Minimum age of primary renter is 25 years old. Proof of age required.

Sep 4 – 11

R2,755 ZAR per night

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 129 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!

May 8 – 15

R2,517 ZAR per night

Guest favorite

Condo in Sarasota

4.97 out of 5 average rating, 166 reviews

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

Beautiful and comfy 2 bedroom/2 bathroom condo that sleeps 4. The condo is located only 1/2 mile from the Gulf Of Mexico. Spacious, comfortable, in a small & quiet complex that provides easy access to restaurants and stores on or off Siesta Key. You'll get super easy Siesta Key access (3 min drive/20 min walk) at a very affordable price in a perfect location to avoid traffic and enjoy the rest of Sarasota when you're not at the beach.

Sep 25 – Oct 2

R2,755 ZAR per night

Guest favorite

Home in Sarasota

4.98 out of 5 average rating, 130 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! :-)

May 11 – 18

R5,165 ZAR per night