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Vacation rentals with a pool in Lido Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lido Key

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

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Home in Longboat Key

4.86 out of 5 average rating, 110 reviews

Summer House longboat key

Luxurious waterfront 3 Bedroom home with bay and and canal view with extra dock that can accommodate up to 21 ft+-heated pool, tropical landscaping with coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach, It is a private home nestled on a canal that is 2 houses from Sarasota Bay. Our home is situated in the desirable quiet neighborhood of Country Club Shore minutes from at Armand’s circle

Condo in Siesta Key

4.96 out of 5 average rating, 296 reviews

WE ARE OPEN—On the Beach; Siesta Key SunBum Studio

WE ARE OPEN POST OCT STORMS :) Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta 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!

Rental unit in Sarasota

4.96 out of 5 average rating, 160 reviews

ROYS PLACE Romantic, Private, Paradise!

NAMED #1 BEST AIRBNB WITH POOL IN SARASOTA BY TRIP 101 TRAVEL GUIDE FOR THREE YEARS. "I LOVE ROYS PLACE!" Words most commonly used by guests in reviews are "quality" "clean" "cute" "sexy" "cool" "safe" . This is a restored 600 sq. ft. one bedroom apartment in an old historic home located in the heart of coveted safe Northwest Sarasota. Offered for you, a romantic boutique apartment with your own private (exclusive to you, not shared) CLOTHING OPTIONAL lanai, outdoor shower and heated pool.

Condo in Sarasota

4.96 out of 5 average rating, 132 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.

Home in Sarasota

4.95 out of 5 average rating, 450 reviews

The Cottage At Central Park

There is no more charming place to stay! From the minute you step inside this immaculate and cozy private residence you will feel right at home. With a beautiful open kitchen, natural light that pours into every room, a spacious back porch overlooking the pool and fenced in yard with a fire pit, this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Rental unit in Sarasota

4.88 out of 5 average rating, 135 reviews

Downtown Apartment w/ Pool, Gym, & Coworking 329

This 2/2 apartment features an oversized kitchen with island, slider with views of Downtown. Primary has a king bed and en-suite bathroom. 2nd bedroom has a twin bed with twin trundle. Shared amenities include: gym; sunset deck; massive roof deck with heated pool; gazebo with big-screen TV, fireplace, wet bar, dog run and access to the adjacent Cowork office space building. Also on-site is Motoneko Cafe, a full-service coffee/ramen shop that also serves tea, espresso drinks, and snacks.

Guest suite in Sarasota

4.93 out of 5 average rating, 307 reviews

Beach & Town Posh Location! Jungle Paradise Studio

PRIME Town/Beach 3.2 miles location! *Private Studio* Access Non shared Pool. Studio w/private entrance & private patio @Designers private Home,Tropical Jungle, like Posh Resort! Quiet, residential area. Sought-after amenities. 10 min/Siesta Beach, shops, dining, & 5mins/Downtown Sarasota. Walk/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!

Condo in Longboat Key

4.98 out of 5 average rating, 170 reviews

Cozy Condo by the Water!

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 loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Guesthouse in Sarasota

4.99 out of 5 average rating, 132 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!

Island in Sarasota

4.97 out of 5 average rating, 317 reviews

New NOV Openings! Sarasota #1 Lux BEACH Villa

BOOK 2024 NOW, and 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!

Rental unit in Sarasota

4.97 out of 5 average rating, 167 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.

Serviced apartment in Siesta Key

4.99 out of 5 average rating, 167 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

BEST SPOT AT SIESTA KEY BEACH. Beautiful apartment in Siesta Key Beach. Fully equipped. Condo hotel, on the best area of the beach in Siesta. Main bedroom with King bed. 2nd room with two single beds. Queen sofa bed in the living room. Pack n Play & high chair for children. 1200 MB Wifi. 70” Smart TV, 2 55” TVs Nesspreso, Keurig.

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Popular amenities for Lido Key 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, 195 reviews

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

Home in Siesta Key

5 out of 5 average rating, 137 reviews

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

Home in Sarasota

4.88 out of 5 average rating, 145 reviews

5 minutes to private Siesta Key Beach + 2 pools

Home in Sarasota

4.92 out of 5 average rating, 102 reviews

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Home in Sarasota

4.98 out of 5 average rating, 124 reviews

Take a Siesta off Bahia Vista

Home in Sarasota

4.82 out of 5 average rating, 225 reviews

Private Siesta Beach House Oasis with Heated Pool.

Home in Siesta Key

4.92 out of 5 average rating, 115 reviews

Siesta Peace Retreat a private home rental

Home in Sarasota

5 out of 5 average rating, 28 reviews

Cozy Boho Bungalow Pool/Spa

Condo rentals with a pool

Condo in Siesta Key

4.93 out of 5 average rating, 192 reviews

Steps away from beach and village! #1 in Siesta!

Condo in Siesta Key

4.93 out of 5 average rating, 105 reviews

Sea Shell Ocean view On Beach Walk everywhere Pool

Condo in Siesta Key

4.96 out of 5 average rating, 112 reviews

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

Condo in Siesta Key

4.91 out of 5 average rating, 218 reviews

Sea Club 2-Relaxing Siesta Key Condo-Siesta Sky

Condo in Siesta Key

4.9 out of 5 average rating, 101 reviews

*Open* Crystal House on Siesta Key Beach

Condo in Sarasota

4.85 out of 5 average rating, 137 reviews

Siesta Key Ground Floor Condo 2BR On Trolley Line

Condo in Bradenton

4.95 out of 5 average rating, 120 reviews

Cozy 2 bed/2.5 bath townhome

Condo in Bradenton Beach

4.87 out of 5 average rating, 114 reviews

Charming and Updated 1 Bedroom in Runaway Bay

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