Vacation rentals with a pool in Saint Armands Key

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Top-rated rentals with a pool in Saint Armands Key

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

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Guest favorite

Apartment in Siesta Key

4.99 out of 5 average rating, 143 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

Dec 14 – 21

G$94,501 GYD per night

Guest favorite

Guest suite in Sarasota

4.94 out of 5 average rating, 287 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 21 – 28

G$38,314 GYD per night

Guest favorite

Guest suite in Sarasota

4.89 out of 5 average rating, 111 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 12 – 19

G$26,107 GYD per night

Guest favorite

Island in Sarasota

4.97 out of 5 average rating, 303 reviews

*NEW May 17 CX 30% OFF! Sarasota #1 Luxury Villa*

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 6 – 13

G$131,439 GYD per night

Guest favorite

Condo in Sarasota

4.96 out of 5 average rating, 121 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 1 – 8

G$31,751 GYD per night

Guest favorite

Condo in Longboat Key

4.97 out of 5 average rating, 150 reviews

Charming Condo on the Coast!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with complimentary chairs and umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Nov 24 – Dec 1

G$65,903 GYD per night

Guest favorite

Guesthouse in Sarasota

5.0 out of 5 average rating, 103 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

Sep 11 – 18

G$28,404 GYD per night

Guest favorite

Guesthouse in Sarasota

4.89 out of 5 average rating, 168 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 3 – 10

G$21,204 GYD per night

Superhost

Condo in Sarasota

4.89 out of 5 average rating, 56 reviews

Steps from Lido Beach & St. Armands Circle

Come getaway and enjoy yourself along with your loved ones or just for a private relaxing break from it all. This One Bedroom/One Bath apartment w/ Lanai(Screened Balcony), and shared Pool/Jacuzzi is located steps from the beautiful Lido Beach, boutique shopping, spa's and incredible dining on St. Armands Circle. If your looking to have everything you need from world famous beaches to historical sites and great food around the corner come and stay!

Jul 28 – Aug 4

G$42,275 GYD per night

Guest favorite

Guesthouse in Sarasota

4.99 out of 5 average rating, 131 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!

Aug 15 – 22

G$27,681 GYD per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 188 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Jul 22 – 29

G$23,285 GYD per night

Guest favorite

Condo in Siesta Key

4.85 out of 5 average rating, 132 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.

Sep 29 – Oct 6

G$31,223 GYD per night