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Holiday rentals with a pool in Siesta Key

Find and book unique homes with a pool on Airbnb

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

9–16 Jan

$203 NZD 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

12–19 Apr

$889 NZD 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!

25 Apr – 2 May

$365 NZD 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

10–17 Jul

$247 NZD 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.

14–19 Jun

$276 NZD per night

Condo in Siesta Key

4.82 out of 5 average rating, 233 reviews

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

We pay your AIRBNB service fees for you! Updated & inviting coastal getaway, located on the island of Siesta Key in a small resort called Solitude Suites on Siesta Key. The “Sunset Suite” has a living/dining/kitchenette area w/ 65” TV, a separate bedroom & a separate bathroom. Off the bedroom is a private open wood deck. Table & chairs allow you to enjoy the perfect view of a Siesta Key sunset. New shower in Dec 2023! 2 min drive or 10 min walk to beach! Enjoy FREE Kayaks, SUPs & Tiki Huts!

10–17 May

$359 NZD 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.

11–18 Dec

$309 NZD 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.

11–18 Jan

$897 NZD per night

Guest favourite

Guesthouse in Sarasota

5.0 out of 5 average rating, 100 reviews

Magical Guesthouse 1 mi from SRQ airport

Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

22–29 Sep

$262 NZD 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!

26 Jun – 3 Jul

$273 NZD 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!

12–19 Dec

$1,148 NZD 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.

5–12 Jun

$237 NZD per night

Holiday 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!

9–16 Dec

$1,716 NZD per night

Guest favourite

Home in Siesta Key

4.9 out of 5 average rating, 105 reviews

Siesta Key, FL - Casa Berano

19–26 Aug

$582 NZD per night

Guest favourite

Home in Sarasota

4.97 out of 5 average rating, 206 reviews

Your private retreat near Siesta Key Beach.

25 Aug – 1 Sep

$671 NZD 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

22–29 Nov

$755 NZD per night

Guest favourite

Home in Sarasota

4.94 out of 5 average rating, 296 reviews

☀Coastal Gem☀Heated pool & amazing location!☀

2–9 Aug

$487 NZD 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!!!

19–26 Sep

$449 NZD per night

Guest favourite

Home in Sarasota

4.97 out of 5 average rating, 109 reviews

Gorgeous Home / Heated Pool and Spa

7–14 Nov

$667 NZD per night

Guest favourite

Home in Siesta Key

4.89 out of 5 average rating, 139 reviews

Siesta Beach House

4–11 Sep

$632 NZD per night

Condo rentals with a pool

Guest favourite

Condo in Siesta Key

4.92 out of 5 average rating, 130 reviews

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

25 May – 1 Jun

$581 NZD per night

Guest favourite

Condo in Longboat Key

4.97 out of 5 average rating, 148 reviews

Charming Condo on the Coast!

14–21 Dec

$627 NZD 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

13–20 Sep

$415 NZD per night

Guest favourite

Condo in Sarasota

4.92 out of 5 average rating, 122 reviews

Beachside Siesta Key Cottage steps from the ocean

28 May – 2 Jun

$589 NZD per night

Guest favourite

Condo in Siesta Key

4.81 out of 5 average rating, 284 reviews

[Beach Elements] pool view + private beach & bikes

16–23 Dec

$750 NZD per night

Condo in Siesta Key

4.82 out of 5 average rating, 131 reviews

The Key to a Great Vacation!

2–9 Nov

$414 NZD per night

Guest favourite

Condo in Siesta Key

4.83 out of 5 average rating, 122 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

4–11 Jan

$827 NZD 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

11–18 Oct

$730 NZD per night

Quick stats about holiday 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
$101 NZD before taxes and fees

Destinations to explore