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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

R1,735 ZAR 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 10 – 17

R2,355 ZAR 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!

Oct 17 – 24

R3,456 ZAR 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

R2,503 ZAR 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!

Nov 5 – 12

R11,857 ZAR 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

R2,544 ZAR per night

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

R3,121 ZAR 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

R2,779 ZAR per night

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.

May 28 – Jun 4

R2,731 ZAR 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!

Jun 26 – Jul 3

R2,516 ZAR per night

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...

Jan 7 – 14

R1,941 ZAR per night

Camper/RV in Sarasota

4.91 out of 5 average rating, 32 reviews

Sandmari RV/ 8 miles to Siesta Key

Stay in our 2023 RV located 8.9 miles from Siesta Key. The RV sits next to our home. We live in a safe neighborhood. We are closed to I 75, beaches, parks, UTC mall, restaurants, stores, etc. The Rv has one queen bed, dining table that collapses in a twin bed. Nice and comfortable place to stay. Kitchen have microwave, oven, stove, rice maker, coffee maker, toaster. We include the use of the pool, fire pit, and outside areas.

Apr 8 – 15

R1,862 ZAR per night

Vacation rentals for every style

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Popular amenities for Sarasota County rentals with a pool

Free parking on premises

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!!!

Sep 19 – 26

R4,020 ZAR per night

Home in Sarasota

4.97 out of 5 average rating, 206 reviews

Your private retreat near Siesta Key Beach.

Apr 15 – 22

R8,212 ZAR per night

Home in Sarasota

4.97 out of 5 average rating, 112 reviews

Take a Siesta off Bahia Vista

Aug 29 – Sep 5

R4,723 ZAR 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

R2,928 ZAR per night

Home in Sarasota

4.97 out of 5 average rating, 116 reviews

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

Oct 14 – 21

R5,715 ZAR per night

Home in Sarasota

4.94 out of 5 average rating, 296 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

Aug 2 – 9

R4,493 ZAR per night

Home in Sarasota

4.93 out of 5 average rating, 106 reviews

Lake Front House with a Pool

Aug 26 – Sep 2

R4,295 ZAR per night

Home in Sarasota

4.97 out of 5 average rating, 159 reviews

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

Aug 19 – 26

R6,558 ZAR per night

Condo rentals with a pool

Condo in Siesta Key

4.87 out of 5 average rating, 209 reviews

Siesta Key Beach Community!

May 18 – 25

R2,361 ZAR 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

R3,846 ZAR per night

Condo in Venice

4.82 out of 5 average rating, 219 reviews

Updated beachy condo - ready for you!

Dec 12 – 19

R2,493 ZAR per night

Condo in Venice

4.83 out of 5 average rating, 174 reviews

Venice Beach Studio 71

Aug 19 – 26

R2,390 ZAR per night

Condo in Sarasota

4.92 out of 5 average rating, 122 reviews

Beachside Siesta Key Cottage steps from the ocean

May 28 – Jun 2

R5,300 ZAR per night

Condo in Sarasota

4.87 out of 5 average rating, 171 reviews

♥ 1/2 mile to BEACH! ➸ KING in master ➸ POOL ♥

Aug 25 – Sep 1

R3,777 ZAR per night

Condo in Sarasota

4.89 out of 5 average rating, 102 reviews

★ NEW ★ Serene Retreat | Private Patio & Pool ★

Sep 14 – 21

R3,739 ZAR per night

Condo in Siesta Key

4.96 out of 5 average rating, 275 reviews

On the Beach; Siesta Key SunBum Studio

Jan 11 – 18

R8,611 ZAR per night

Destinations to explore