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Vacation rentals with a pool in Siesta Key

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Top-rated rentals with a pool in Siesta Key

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

$165 CAD per night

Guest favourite

Apartment in Siesta Key

4.99 out of 5 average rating, 141 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Beautiful Apartment w/ Hotel Services, at Siesta Key Beach. Totally remodeled. Fully equipped to spend the best holidays with family or friends. Condo hotel, on the best beach in Siesta. Beach pool, shade pool (heated), gym, 3 tennis courts on site (2 clay, 1 hard) and 2 pickle ball courts. Master bedroom with King bed. The Mattress is a SAATVA ORGANIC. 2nd room with 2 single beds, and a queen sofa bed, in the living room. Pack n Play 600 MB Wifi. HD TV. 70” Smart TV Nesspreso, Keurig Machines

Apr. 12 – 19

$723 CAD per night

Guest favourite

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

$297 CAD per night

Guest favourite

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

$201 CAD per night

Guest favourite

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

$225 CAD per night

Guest favourite

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

$251 CAD per night

Guest favourite

Condo in Siesta Key

4.96 out of 5 average rating, 275 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Mar. 9 – 16

$730 CAD per night

Guest favourite

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

$223 CAD per night

Guest favourite

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

$336 CAD per night

Guest favourite

Home in Siesta Key

5.0 out of 5 average rating, 124 reviews

One-of-a-kind*Beach, Village, Dock & Private Pool!

HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time. If you want a cute, private original bungalow style beach cottage home all to yourself without the shared wall feel of a condo, then you are in the right spot!

Dec. 12 – 19

$934 CAD per night

Guest favourite

Condo in Siesta Key

4.87 out of 5 average rating, 209 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. 11 – 18

$193 CAD per night

Guest favourite

Condo in Siesta Key

4.85 out of 5 average rating, 131 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

A cozy Siesta Key ground floor condo unit w 2 bedrooms & 1 bath on the trolley line. Has all the amenities you need for a relaxing beach vacation and your day at the beach. Located conveniently to Crescent beach w access to the south and Siesta Key public beach to the north. Trolley stops right out front. Assigned parking spot directly in front of the unit.

Nov. 6 – 13

$278 CAD per night

Vacation rentals for every style

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Popular amenities for Siesta Key rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Siesta Key

4.87 out of 5 average rating, 119 reviews

"Safe & Clean" Palm Oasis - Relax in comfort!

Dec. 9 – 16

$1,395 CAD per night

Guest favourite

Home in Sarasota

4.94 out of 5 average rating, 296 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

Aug. 2 – 9

$389 CAD per night

Guest favourite

Home in Siesta Key

4.9 out of 5 average rating, 105 reviews

Siesta Key, FL - Casa Berano

Aug. 19 – 26

$473 CAD per night

Guest favourite

Home in Sarasota

4.97 out of 5 average rating, 109 reviews

Gorgeous Home / Heated Pool and Spa

Sep. 24 – Oct. 1

$515 CAD per night

Guest favourite

Home in Siesta Key

4.89 out of 5 average rating, 139 reviews

Siesta Beach House

Sep. 29 – Oct. 6

$514 CAD per night

Guest favourite

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

$365 CAD per night

Guest favourite

Home in Sarasota

4.97 out of 5 average rating, 206 reviews

Your private retreat near Siesta Key Beach.

May 15 – 22

$522 CAD per night

Guest favourite

Home in Sarasota

4.87 out of 5 average rating, 132 reviews

5 minutes to private Siesta Key Beach + 2 pools

Apr. 8 – 15

$737 CAD per night

Condo rentals with a pool

Condo in Siesta Key

4.82 out of 5 average rating, 233 reviews

Siesta Key 1/1 King bed “Sunset Suite” Pool Kayaks

May 10 – 17

$292 CAD per night

Guest favourite

Condo in Sarasota

4.89 out of 5 average rating, 127 reviews

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

Oct. 22 – 29

$251 CAD per night

Guest favourite

Condo in Sarasota

4.95 out of 5 average rating, 123 reviews

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

Sep. 13 – 20

$337 CAD per night

Guest favourite

Condo in Siesta Key

4.92 out of 5 average rating, 130 reviews

*A Stones Throw from #1 Voted Siesta Key Beach*

May 24 – 31

$471 CAD per night

Guest favourite

Condo in Longboat Key

4.97 out of 5 average rating, 148 reviews

Sunset Views - Open May 13 & 14 - $175/nt!

Apr. 6 – 13

$510 CAD per night

Guest favourite

Condo in Siesta Key

4.96 out of 5 average rating, 103 reviews

2 Bed/2 Bath Condo Resort View on Siesta Key Beach

Oct. 10 – 17

$594 CAD per night

Guest favourite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Dec. 14 – 21

$211 CAD per night

Condo in Siesta Key

4.82 out of 5 average rating, 131 reviews

The Key to a Great Vacation!

Nov. 2 – 9

$337 CAD per night

Quick stats about vacation rentals with a pool in Siesta Key

Total rentals
1.3K properties
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Pet-friendly rentals
220 properties allow pets
Family-friendly rentals
1K properties are a good fit for families
Total number of reviews
22K reviews
Nightly prices starting at
$82 CAD before taxes and fees

Destinations to explore