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Vacation rentals with a pool in Sarasota County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sarasota County

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

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Condo in Sarasota

4.8 out of 5 average rating, 199 reviews

Near beach. Pool view. King bed. Daily rentals

The ‘pool view’ overlooks the swimming pool & has a private covered porch for shade 1 bed 1 bath w/ private entrance. The bedroom has a king sized Tempurpedic mattress bed. The living room has a kitchenette area with a fridge, freezer, microwave, coffee maker and the essentials. There is a HD smart TV with cable and apps. Separate bedroom with King size Tempurpedic bed 3 mins walk to Crescent beach access You can walk to a great choice of places to eat and drink Max 2 guests No smoking, pets

Jan 9 – 16

G$19,288 GYD per night

Guest suite in Sarasota

4.89 out of 5 average rating, 109 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 14 – 21

G$26,176 GYD per night

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!

Jan 18 – 25

G$38,416 GYD per night

Apartment in Sarasota

4.96 out of 5 average rating, 206 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 14 – 19

G$27,823 GYD per night

Island in Sarasota

4.97 out of 5 average rating, 301 reviews

NEW MAY CX! last min SALE Sarasota #1 Luxury!

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!

Jan 8 – 15

G$131,790 GYD per night

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 11 – 18

G$31,836 GYD per night

Guesthouse in Englewood

4.97 out of 5 average rating, 202 reviews

Shabby chic cottage with pool one mile from beach

This adorable shabby chic decor style studio cottage for 2 is located on one acre of old Florida landscaping. Great area for walking, biking, for exercise. Included with this home is access to a pool and large, lovely lanai, just outside the door. Head south for 7 min to historic Dearborn St or north for 3 miles to Venice. This location offers peace and tranquility combined with accessibility to endless activities nearby. 2 twins OR one King, per your preference. The pool is unheated.

Apr 16 – 23

G$28,281 GYD per night

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.

Jun 5 – 12

G$30,885 GYD per night

Apartment in Sarasota

4.97 out of 5 average rating, 94 reviews

Luxury Large Studio, private kitchen and bathroom

Luxury specious furnished attached studio with king size bed, kitchenette and bathroom. Includes: utilities, garbage and Wi-Fi, Netflix, Hulu. There are stairs (3 steps) to get to the house. Private entrance but shared outside area, outside laundry, driveway parking on premises. Located in South Sarasota on one acre, very QUIET and private... resort like setting! Small Pool, gazebo, hammock, beautiful landscaping 10-15 minutes to Siesta Key Beach by car Quiet animal is OK No smoking

May 22 – 29

G$20,366 GYD per night

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!

Nov 4 – 11

G$28,130 GYD per night

Home in Sarasota

4.97 out of 5 average rating, 159 reviews

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

"The Palms" is a single-family home with heated private pool in the heart of Sarasota. The home is 5 miles to the #1 beach in the USA, Siesta Key Beach. It offers 3 bedrooms, 2 bathrooms with a screened-in outdoor sunroom. The fully private, fully enclosed outdoor space is one-of-a-kind with a modern pool, hot tub, BBQ grill, fire pit, beach bar, outdoor TV & lounge chairs for families or snowbirds to enjoy Florida outdoor living in style!

May 9 – 16

G$40,465 GYD per night

Apartment in Sarasota

4.97 out of 5 average rating, 166 reviews

Gillespie On The Park, Walk to Downtown

Contemporary Studio apartment with balcony above garage. Studio is half block from Gillespie Park with its public walking/jogging/biking paths, tennis courts, basketball court, and retention pond. Within walking distance to downtown and Rosemary District: restaurants, shops, movie theaters, cultural events, Whole Food Market, Starbucks etc.

Oct 19 – 26

G$18,464 GYD per night

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Popular amenities for Sarasota County rentals with a pool

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Air conditioning

House rentals with a pool

Home in Sarasota

4.95 out of 5 average rating, 181 reviews

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

Aug 29 – Sep 5

G$44,683 GYD per night

Home in Sarasota

4.97 out of 5 average rating, 206 reviews

Your private retreat near Siesta Key Beach.

May 15 – 22

G$65,027 GYD per night

Home in Sarasota

4.97 out of 5 average rating, 112 reviews

Take a Siesta off Bahia Vista

Aug 22 – 29

G$52,498 GYD per night

Home in Sarasota

4.81 out of 5 average rating, 107 reviews

1 House 1400sq. ft. 12 min from Siesta Key!

Dec 12 – 19

G$38,987 GYD per night

Home in Venice

4.88 out of 5 average rating, 182 reviews

Perfect vacation home 3 miles from beach.

Oct 27 – Nov 3

G$32,547 GYD per night

Home in Sarasota

4.94 out of 5 average rating, 296 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

Aug 2 – 9

G$49,933 GYD per night

Home in Sarasota

4.97 out of 5 average rating, 116 reviews

Gorgeous Pool House 3BR/2BA near Siesta Key Beach

Aug 2 – 9

G$63,518 GYD per night

Home in Venice

4.89 out of 5 average rating, 161 reviews

Venice Pool Villa with Bikes Kayaks Great Beaches!

Sep 21 – 28

G$30,548 GYD per night

Condo rentals with a pool

Condo in Siesta Key

4.87 out of 5 average rating, 209 reviews

Siesta Key Beach Community!

Jun 11 – 18

G$26,246 GYD per night

Condo in Sarasota

4.95 out of 5 average rating, 123 reviews

Cozy Beach Side 1BD/2BA, Walk to Beach & Pool

Sep 13 – 20

G$42,743 GYD per night

Condo in Venice

4.82 out of 5 average rating, 219 reviews

Updated beachy condo - ready for you!

Dec 12 – 19

G$27,713 GYD per night

Condo in Venice

4.83 out of 5 average rating, 174 reviews

Venice Beach Studio 71

Aug 18 – 25

G$26,562 GYD per night

Condo in Sarasota

4.89 out of 5 average rating, 127 reviews

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

Apr 19 – 26

G$38,703 GYD per night

Condo in Sarasota

4.92 out of 5 average rating, 122 reviews

Beachside Siesta Key Cottage steps from the ocean

Jul 16 – 23

G$52,170 GYD per night

Condo in Sarasota

4.97 out of 5 average rating, 166 reviews

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

Dec 7 – 14

G$36,317 GYD per night

Condo in Sarasota

4.89 out of 5 average rating, 102 reviews

★ NEW ★ Serene Retreat | Private Patio & Pool ★

Sep 14 – 21

G$41,553 GYD per night

Destinations to explore