Longboat Key Vacation Rentals

Merry Mermaid Tree House

Almost Beachfront, private pool/spa backyard oasis, Gulf views!

Merry Mermaid Tree House

3 Bedrooms
3 Bathrooms
$1000 - $1299 / night
(excl. fees & taxes)
Featured
Craig House with Heated Pool

Craig House with Heated Pool

Craig House with Heated Pool

2 Bedrooms
2 Bathrooms
82
$156 - $205 / night
(excl. fees & taxes)
Featured
Anna Maria Island - Azure Bliss Vacation Home

Anna Maria Island - 3Bed 2Bath Home - Private Heated Pool - Walk to Beach

Anna Maria Island - Azure Bliss Vacation Home

3 Bedrooms
2 Bathrooms
21
$450 - $500 / night
(excl. fees & taxes)
Tropical Beach Condo!

Available This Sunday - Wednesday!

Tropical Beach Condo!

1 Bedroom
1 Bathroom
11
$225 - $300 / night
(excl. fees & taxes)
Longboat Breeze

Luxury Home on the Water, Pet Friendly with a Pool

Longboat Breeze

3 Bedrooms
2½ Bathrooms
$209 - $923 / night
(excl. fees & taxes)
The Aquamarine Dream on Longboat Key

Angler's Cove - Private Dock and Boat Lift

The Aquamarine Dream on Longboat Key

3 Bedrooms
2 Bathrooms
$207 - $1005 / night
(excl. fees & taxes)
Turtle Crawl Inn 63

Beach Front Condo Paradise. Ground Floor. Studio.

Turtle Crawl Inn 63

0 Bedroom
1 Bathroom
17
$189 - $265 / night
(excl. fees & taxes)
Turtle Crawl Inn 64

Beach Front One Bedroom Condo Paradise. Fully Remodeled September 2021.

Turtle Crawl Inn 64

1 Bedroom
1 Bathroom
$225 - $340 / night
(excl. fees & taxes)
Panoramic Gulf View with Amazing Sunset.

Spacious Condo, 1 huge Bedroom, 2 very comfortable Queen beds. One Sofa sleeper in the living room. What you see is what you get to view every day.

Panoramic Gulf View with Amazing Sunset.

1 Bedroom
1 Bathroom
134
$265 - $440 / night
(excl. fees & taxes)
Linley St. Cottage

Classic 'Old Style Florida' home in historic Longbeach Village

Linley St. Cottage

3 Bedrooms
2 Bathrooms
16
$143 / night
(excl. fees & taxes)
Mable's Place

Mable's Place ~ A Historic "Old" Florida Cottage

Mable's Place

2 Bedrooms
2 Bathrooms
$210 / night
(excl. fees & taxes)
Beach Condo with Pool - Soak Up the Sun!

Relax

Beach Condo with Pool - Soak Up the Sun!

1 Bedroom
1 Bathroom
122
$199 - $300 / night
(excl. fees & taxes)
Bayside Escape

Bayside Escape- 4 BR Pool Home w/Bay View!

Bayside Escape

4 Bedrooms
3½ Bathrooms
$199 / night
(excl. fees & taxes)
Sweet Escape

Pool bball gym near beach & IMG

Sweet Escape

5 Bedrooms
4 Bathrooms
$700 - $2200 / night
(excl. fees & taxes)
Sandcastle Dreams

Elegant Beachfront Condo on Anna Maria Island

Sandcastle Dreams

3 Bedrooms
2 Bathrooms
47
$800 / night
(excl. fees & taxes)
Beach Daze at Sandcastle Resort

Amazing Beach front Condo on Anna Maria Island! Views of the Sunset from every room!

Beach Daze at Sandcastle Resort

3 Bedrooms
2 Bathrooms
36
$800 / night
(excl. fees & taxes)
Pool Home with Easy Drive to Beaches of Anna Maria

saltwater pool, hot tub, located 4 miles from beaches

Pool Home with Easy Drive to Beaches of Anna Maria

3 Bedrooms
2 Bathrooms
20
$379 - $399 / night
(excl. fees & taxes)
Our 3 Suns

Spacious 3 Bedroom, 2 1/2 bath Condo, Steps to the beach! 2 pools, Hot tub & gym

Our 3 Suns

3 Bedrooms
2 Bathrooms
$350 / night
(excl. fees & taxes)
Private Pool Paradise 5 miles to Beaches Sleeps 10

Private Pool Paradise 5 miles to Beaches Sleeps 8

Private Pool Paradise 5 miles to Beaches Sleeps 10

3 Bedrooms
2 Bathrooms
7
$275 / night
(excl. fees & taxes)
Gulf Coast Destination

Enjoy Florida's Gulf Coast with Gulf views, a pool, just a mile to Beautiful Anna Maria Island

Gulf Coast Destination

2 Bedrooms
1 Bathroom
$175 / night
(excl. fees & taxes)
Your Tropical Paradise Destination

Your Tropical Paradise Destination

Your Tropical Paradise Destination

2 Bedrooms
1 Bathroom
29
$150 / night
(excl. fees & taxes)
Backyard wonderland

Zen Tropical Retreat near Anna Maria: Heated Pool, Firepit, Koi Pond, Gazebo

Backyard wonderland

4 Bedrooms
2½ Bathrooms
$417 - $1514 / night
(excl. fees & taxes)
Wilder's West Bradenton

Welcome to Wilder's West Bradenton. 15 Minutes to Anna Maria Island and even closer to Downtown Bradenton's museums, restaurants and bars!

Wilder's West Bradenton

4 Bedrooms
2 Bathrooms
72
$275 / night
(excl. fees & taxes)
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