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Holiday rentals with a pool in Longboat Key

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Top-rated rentals with a pool in Longboat 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

Guest favourite

Apartment in Holmes Beach

4.98 out of 5 average rating, 115 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

Guest favourite

Guest house in Sarasota

5 out of 5 average rating, 151 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger 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

Guest favourite

Apartment in Longboat Key

4.91 out of 5 average rating, 160 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Guest favourite

Apartment in Longboat Key

4.99 out of 5 average rating, 112 reviews

Silver Sands - Winter Availability!

This charming seaside condo 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 one-bedroom condo is optimal for sunset viewing from a private, screened 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 Silver Sands Gulf Beach Resort!

Guest favourite

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!

Guest favourite

Apartment in Bradenton Beach

4.87 out of 5 average rating, 114 reviews

Charming and Updated 1 Bedroom in Runaway Bay

Our charming 1 BR/ 1 Bath condo is a new to the rental market. It was formerly owner occupied. The property is in the Bradenton Beach area of Anna Maria Island. Beach is right across the street with deeded access. The pool is the largest heated pool on the island. Fitness center has newer equipment. There is a fishing pier which also works as a great way to enjoy beautiful views of the Anna Maria sound. Free trolley stop is right in front of the property. Washer/dryer in unit.

Guest favourite

Home in Bradenton Beach

4.97 out of 5 average rating, 159 reviews

BACK Jan 1! Newly Renovated! STEPS 2 Private Beach

NEW Pics Coming! Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Guest favourite

Guest suite in Bradenton

5 out of 5 average rating, 216 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.

Guest favourite

Cottage in Anna Maria

4.96 out of 5 average rating, 224 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Guest favourite

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!

Guest favourite

Apartment in Siesta Key

4.94 out of 5 average rating, 190 reviews

Siesta key getaway!

perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

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Popular amenities for Longboat Key rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Holmes Beach

4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

Guest favourite

Home in Holmes Beach

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 19 reviews

5 min walk to beach, private pool & spa, elevator

Guest favourite

Home in Holmes Beach

4.95 out of 5 average rating, 94 reviews

The Peachy Beach House, steps to the gulf

Guest favourite

Home in Anna Maria

4.99 out of 5 average rating, 102 reviews

1 block to Beach on Pine Ave! Private Pool Oasis

Home in Sarasota

4.82 out of 5 average rating, 225 reviews

Private Siesta Beach House Oasis with Heated Pool.

Guest favourite

Home in Lido Key

5 out of 5 average rating, 16 reviews

Walk to Lido Beach &St. Armands -grill/HEATED POOL

Guest favourite

Home in Bradenton

4.89 out of 5 average rating, 104 reviews

Amazing Game Room-86°Pool/Spa-Beaches-Dog Friendly

Apartment rentals with a pool

Guest favourite

Apartment in Siesta Key

4.83 out of 5 average rating, 209 reviews

No Damage: Cozy 1BR Beach Condo on Siesta Key!

Guest favourite

Apartment in Indian Shores

4.99 out of 5 average rating, 108 reviews

Tropical Beachfront Penthouse-Beach Cottages II

Apartment in Sarasota

4.89 out of 5 average rating, 110 reviews

6 min. from Siesta Beach+heated pool+lake view

Guest favourite

Apartment in Treasure Island

4.99 out of 5 average rating, 168 reviews

Spectacular beach to bay views from this resort.

Guest favourite

Apartment in Bradenton Beach

4.86 out of 5 average rating, 103 reviews

Oceanfront Condo for Beach Lovers

Guest favourite

Apartment in Siesta Key

4.93 out of 5 average rating, 222 reviews

Private Siesta Key Escape

Guest favourite

Apartment in Bradenton

4.95 out of 5 average rating, 149 reviews

The Seashell Cottage with peaceful water views!

Guest favourite

Apartment in Siesta Key

4.94 out of 5 average rating, 152 reviews

Sea Club 2-Relaxing Siesta Key Condo-Mermaids Rest

Quick stats about holiday rentals with a pool in Longboat Key

Total rentals
740 properties
Nightly prices starting at
$54 SGD before taxes and fees
Total number of reviews
6.6K reviews
Family-friendly rentals
590 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
230 properties have a dedicated workspace

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