Location

Dates

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Vacation rentals in Longboat Key, Florida, United States

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

Heated Pool • 9BR/Sleeps32• Pickle/Basketball • Theater

9 bedrooms·3 baths

Bradenton • Florida

$875 – $4.500/ noite(excl. taxas & impostos)

Cozy coastal living with Smart TV & relaxing vibe

Lido Beach Pool & Pavilion, The 25-meter lap pool is open Friday through Sunday, from 10:00 am to 4:30 pm, weather permitting. Fees apply.

Primary queen suite with private ensuite and plenty of natural light

Sunny dining area for morning coffee or family dinners

Lido Key | Steps to Beach, Walk to St. Armands

2 bedrooms·2 baths

Sarasota • Florida

4.97(39 reviews)

$ 1.168,00 USD total por 3 noites

24 – 27 de set. de 2026

Main living room with ample seating, dining today and bright sunshine gracing the windows.

Move the additional seating over to the couch after sitting down for dinner.

Dinner for 4. Quick and easy access to the full size kitchen for home cooked meals while on vacay.

Queen bed, with additional ceiling fans if you like it really cold and of course your very own private full bathroom. Also, ample closet space to fully stretch out.

Lido Key Beach Escape | 2 Private Suites

2 bedrooms·2 baths

Sarasota • Florida

4.95(21 reviews)

$ 1.474,96 USD total por 3 noites

24 – 27 de set. de 2026

Pompano Palms

3 bedrooms·3½ baths

Palmetto • Florida

$71/ noite(excl. taxas & impostos)

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

Art Deco Masterpiece High Season Multi-Month

2 bedrooms·2 baths

Sarasota • Florida

$ 31.480,00 USD total por 120 noites

24 de set. de 2026 – 22 de jan. de 2027

32” TV with streaming device Comfortable couch.

Kitchen, diningroom, livingroom area

Gulf Coast Paradise Hideaway

Queen bed, night stand with usb plug, and lamp. 32”TV with streaming device sits on top of Armoire with plenty of storage. Bedroom does have closet with hangers.

Gulf Coast Paradise Hideaway

Gulf Coast Paradise Hideaway

1 bedroom·1 bath

Palmetto • Florida

$ 989,85 USD $ 911,32 USD total por 7 noites

24 de set. – 1 de out. de 2026

Dinning room and kitchen

Fully stocked kitchen

Full stocked kitchen

Full stocked kitchen

Tropical Escape Sarasota

3 bedrooms·2 baths

Sarasota • Florida

$ 2.130,00 USD total por 7 noites

24 de set. – 1 de out. de 2026

Stunning Gulf Views, Elevator to All Floors, Mini Golf, Heated Pool/Spa

Fun in the sun starts here - Hosted by RentAnnaMaria

Sunset Views from Shore to Please! - Hosted by RentAnnaMaria

Shore to Please - Hosted by RentAnnaMaria

Amazing Views! Main Living Space (3rd Floor) - Elevator to All Floors - Hosted by RentAnna Maria

Shore to Please

5 bedrooms·4½ baths

Anna Maria • Florida

5(13 reviews)

$ 3.608,09 USD total por 4 noites

8 – 12 de nov. de 2026

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

Hubbel Hideaway

4 bedrooms·3 baths

Bradenton • Florida

$ 1.502,00 USD total por 3 noites

29 de set. – 2 de out. de 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Villa Blanca | Luxury 5BR Pool Home on Siesta Key

5 bedrooms·4 baths

Sarasota • Florida

5(2 reviews)

$ 10.632,14 USD $ 10.136,19 USD total por 7 noites

19 – 26 de dez. de 2026

Perfect place to relax, read a book, and cool down with a dip in crystal clear pool with water fall feature

Sun Soaked Paradise - Heated Pool image 2

Front entry way

Sun Soaked Paradise - Heated Pool image 5

Sun Soaked Paradise - Heated Pool

3 bedrooms·2 baths

Bradenton • Florida

$ 980,00 USD total por 3 noites

24 – 27 de set. de 2026

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

Golf Course Condo

2 bedrooms·2 baths

Sarasota • Florida

$116/ noite(excl. taxas & impostos)

Palmetto House

3 bedrooms·3 baths

Sarasota • Florida

$ 2.245,76 USD $ 2.049,86 USD total por 7 noites

26 de set. – 3 de out. de 2026

350 feet of waterfront and a pair that extended out 250 feet into the river.

The house all lite up at night. Very peaceful

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

The Blue Heron Riverfront Retreat

4 bedrooms·4 baths

Ellenton • Florida

5(3 reviews)

$ 3.433,00 USD total por 5 noites

24 – 29 de set. de 2026

FlipFlopsOn III Vacation Rental • 3 Blocks to the water • FL’s Gulf Coast • Sleeps 6

Your boutique Mediterranean-style 2BR bungalow (4 beds) — resort level comfort + coastal charm!

Your own private resort — located on a serene palm-lined lain in Sarasota’s coveted coastal district!

Half a mile to the Siesta Key, home of Siesta Key Beach — experience the sugar white sands of America’s #1 beach!

A Mediterranean-meets-California retreat where natural textures and curated details invite beautiful living

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Gulf

2 bedrooms·1 bath

Sarasota • Florida

5(2 reviews)

$ 2.384,30 USD total por 7 noites

24 – 31 de out. de 2026

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

Sarasota vacation rental

3 bedrooms·2 baths

Sarasota • Florida

$100/ noite(excl. taxas & impostos)

Landscape lighting and firepit in the front of the house

View of the canal in the back of the house

Sunrise over the pool and covered outdoor seating.

Large pull out sectional facing the fireplace and flatscreen TV

Living room with pull out couch, flatscreen and dining table

Tropi-Casa

4 bedrooms·2 baths

Bradenton • Florida

$ 862,50 USD total por 3 noites

24 – 27 de set. de 2026

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

Village Canal home short walk to Beach with pool

3 bedrooms·2 baths

Siesta Key • Florida

5(26 reviews)

$ 14.950,00 USD total por 28 noites

15 de abr. – 13 de mai. de 2027

Welcome to your private paradise just minutes from the beach—where relaxation begins the moment you pull in.

Big group? No problem. Our extendable dining table fits up to 10—perfect for family feasts, card nights, or celebratory toasts.

Get the best of both worlds: soft and firm pillows, a private ensuite, blackout blinds for restful sleep, and a king bed made for unwinding. Plus, a smart TV for ultimate relaxation.

When the beach is a few blocks away but the pool is right here. Welcome to the best of both worlds.

Skip the restaurants (if you want to). This kitchen’s got everything: oven, microwave, fridge, dishwasher—even a TV so you don’t miss a moment.

Siesta Key Home | Heated Pool, Theater & Arcade

4 bedrooms·3 baths

Siesta Key • Florida

5(36 reviews)

$ 3.564,33 USD total por 3 noites

24 – 27 de set. de 2026

Heated Saltwater Pool

The pool and surrounding area features enough lighting to enjoy the Florida evenings in style!

Catch the game on the 75" TV from the HOT TUB!

Newly remodeled kitchen with new stainless steel appliances (refrigerator, induction cook top, built in microwave/oven and dishwasher).

Living Room featuring a large sectional sofa and a 55" smart TV. Sit and enjoy the abundance of natural light.

The Funky Fish House

2 bedrooms·2 baths

Sarasota • Florida

4.99(156 reviews)

$ 1.581,74 USD total por 5 noites

24 – 29 de set. de 2026

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 1

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 2

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 3

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 4

Lovely room 5 miles from Siesta Key w/ Pool & Spa! image 5

Lovely room 5 miles from Siesta Key w/ Pool & Spa!

1 bedroom·1 bath

Sarasota • Florida

4.87(60 reviews)

$ 225,00 USD total por 3 noites

4 – 7 de out. de 2026

you never have to cover the windows, it's a private yard.

Pool view from the dining area

TOP WORLD BEACH AND #1 US BEACH

my favorite yellow lifeguard shack. LET'S GO VISIT>>>>> Are you coming????

#1 Siesta Key Beach Glass House w/supplies

2 bedrooms·2 baths

Siesta Key • Florida

4.64(58 reviews)

$ 2.062,25 USD total por 7 noites

26 de set. – 3 de out. de 2026

Cozy Room 5 miles from beaches! image 1

Cozy Room 5 miles from beaches! image 2

Cozy Room 5 miles from beaches! image 3

Cozy Room 5 miles from beaches! image 4

Cozy Room 5 miles from beaches! image 5

Cozy Room 5 miles from beaches!

1 bedroom·1 bath

Sarasota • Florida

4.95(75 reviews)

$ 225,00 USD total por 3 noites

26 – 29 de set. de 2026

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 3

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 2

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 1

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 4

Villa Blanca | Luxury 5BR Pool Home on Siesta Key image 5

Blanca Cottage| Private 2BR Pool Home Near Siesta

2 bedrooms·2 baths

Siesta Key • Florida

5(2 reviews)

$ 13.392,70 USD total por 14 noites

12 – 26 de dez. de 2026