Location

Dates

Guests

Vacation rentals in Longboat Key, Florida, United States

Stunning modern beach retreat

Oversized heated L-shaped pool

Welcome to Jungalow Beach

Step into paradise

Open-air lanai by the pool

Jungalow Beach

4 bedrooms·6½ baths

Anna Maria • Florida

8742,12 $ USD total por 7 noites

29/11/2026 – 06/12/2026

Take a dip to cool off

Your luxury vacation awaits

Bright hallway with curated island décor

Coastal curb appeal meets modern luxury

Sun and Spring

3 bedrooms·2½ baths

Anna Maria • Florida

3956,58 $ USD total por 7 noites

27/11/2026 – 04/12/2026

This is what backyard fun looks like!

No houses between you and the water

Modern, elevated home

Right across the street from the Bay beach

Welcome to Sand Trap!

Sand Trap

4 bedrooms·4 baths

Anna Maria • Florida

6328,43 $ USD total por 7 noites

18/01/2027 – 25/01/2027

Private heated pool and spacious fenced backyard with artificial turf, colorful seating, and an outdoor dining area.

Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

Bradenton Getaway | Pool & BBQ | Near the Island

3 bedrooms·2 baths

Bradenton • Florida

1258,00 $ USD total por 3 noites

18/11/2026 – 21/11/2026

Heated pool & spa

Bathroom 1 bath/shower

Bathroom 2 walk in shower

Heated Pool & Spa 3bd/2bth, near Siesta Key Beach

3 bedrooms·2 baths

Sarasota • Florida

$120 – $360/ noite(excl. taxas & impostos)

Relaxing saltwater pool area ideal for all-day lounging

Resort-style saltwater pool perfect for cooling off

Inviting retreat with room for friends and family to relax

Welcome to Manatee Manor

Manatee Manor

3 bedrooms·2 baths

Anna Maria • Florida

3433,47 $ USD total por 7 noites

28/11/2026 – 05/12/2026

Beautiful private backyard with pool

Sparkling private heated pool

Welcome to Idyll Tides!

Short walk to Bean Point

Idyll Tides

3 bedrooms·2 baths

Anna Maria • Florida

3177,45 $ USD total por 7 noites

29/11/2026 – 06/12/2026

Canalfront paradise awaits

Private tropical backyard oasis

Welcome to Iris-istible Options

Your coastal escape begins here

Iris-istible Options

4 bedrooms·3 baths

Anna Maria • Florida

3955,35 $ USD total por 7 noites

28/11/2026 – 05/12/2026

Your own private slice of island calm

Sparkling pool steps from the water

Welcome to Anna Belle

Step inside to light, warmth, and modern coastal style

Open, airy entry that sets the tone for your stay

Anna Belle

3 bedrooms·3 baths

Anna Maria • Florida

5(1 review)

4611,39 $ USD total por 7 noites

29/11/2026 – 06/12/2026

Dinning room and kitchen

Fully stocked kitchen

Full stocked kitchen

Full stocked kitchen

Tropical Escape Sarasota

3 bedrooms·2 baths

Sarasota • Florida

2130,00 $ USD total por 7 noites

18/11/2026 – 25/11/2026

Beautiful huge saltwater pool

So close to the beach

Newly remodeled coastal home

Dining area with a view!

Jacaranda Gem

3 bedrooms·2½ baths

Anna Maria • Florida

5(1 review)

4095,66 $ USD total por 4 noites

08/05/2027 – 12/05/2027

Heated private pool

Welcome to Hook Wine and Sinker

Spacious elevated 4 bedroom home

Hook Wine and Sinker

4 bedrooms·2½ baths

Anna Maria • Florida

5(2 reviews)

3955,35 $ USD total por 7 noites

02/12/2026 – 09/12/2026

Drift into island relaxation by the water

Blue-water bliss with swaying palms above

Dip your toes while you unwind in style

Welcome to Jungalow Bay

Jungalow Bay

3 bedrooms·3 baths

Anna Maria • Florida

5(1 review)

4007,86 $ USD total por 7 noites

28/11/2026 – 05/12/2026

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)

2886,30 $ USD total por 4 noites

06/12/2026 – 10/12/2026

Enjoy your waterfront pool and spa

Direct beachfront home - No Tan Lines

Elevated beachfront home with pool

Welcome to No Tan Lines!

No Tan Lines

4 bedrooms·4 baths

Anna Maria • Florida

11 011,81 $ USD total por 7 noites

11/12/2026 – 18/12/2026

Welcome to Paradise

Private tropical oasis

Convenient ground level home

Charming beach house

Paradise Pointe

3 bedrooms·2 baths

Anna Maria • Florida

3433,47 $ USD total por 7 noites

28/11/2026 – 05/12/2026

Private heated pool

Whispering Winds by Beach Boutique Rentals

Steps to the Bay!

Stylish living area

Full of character and charm!

Whispering Winds

2 bedrooms·2 baths

Anna Maria • Florida

5(5 reviews)

3282,07 $ USD total por 7 noites

28/11/2026 – 05/12/2026

Refreshing dips under open skies

Game room by the pool

Welcome to Pelican Place

Bright and welcoming island retreat

Pelican Place

3 bedrooms·2 baths

Anna Maria • Florida

3557,78 $ USD total por 7 noites

05/12/2026 – 12/12/2026

White Palms gorgeous pool

Welcome to White Palms

Ground level north end home!

Welcoming entryway

Adorable details

White Palms

3 bedrooms·2 baths

Anna Maria • Florida

3614,40 $ USD total por 7 noites

06/12/2026 – 13/12/2026

A pool unlike any other

Fun beyond the beach awaits

Welcome to Beachfront Bliss

Welcome to unforgettable island living

Open living area made for gathering

Beachfront Bliss

5 bedrooms·5½ baths

Anna Maria • Florida

11 811,86 $ USD total por 7 noites

28/11/2026 – 05/12/2026

Secluded backyard

Private saltwater pool

So close to the beach!

Bliss by the Beach- Beach Boutique Rentals

Beautiful and open kitchen

Bliss by the Beach

2 bedrooms·2 baths

Anna Maria • Florida

3787,95 $ USD total por 5 noites

05/06/2027 – 10/06/2027

Experience luxury!

Beautiful backyard at any time of the day

Amazing views from the top deck

Almost bay front location

Pier to Pier Paradise

4 bedrooms·4½ baths

Anna Maria • Florida

5244,05 $ USD total por 7 noites

28/11/2026 – 05/12/2026

Sunny Limelight pool

See how close you are to the beach

Welcome to Limelight!

Bright open living space

Limelight

3 bedrooms·2 baths

Anna Maria • Florida

3439,62 $ USD total por 7 noites

04/12/2026 – 11/12/2026

Poolside backyard retreat

Kick back and relax poolside

Welcome to Bay Bungalow

Step inside the open living space

Recently updated interior with new furniture

Bay Bungalow

3 bedrooms·2 baths

Anna Maria • Florida

2976,82 $ USD total por 7 noites

29/11/2026 – 06/12/2026