Siesta Key Vacation Rentals

Icon
Icon
Gulf-to-Bay Living on Longboat Key
Icon

Waterfront condo paradise. Island living. Ground floor. 2 Bd, 2 Ba. Private harbour community, 4 heated pools, Gulf-front pavilion.

2 Bedrooms
2 Bathrooms
$180 / night (excl. fees & taxes)
Icon
Icon
Golf Course Condo
Icon

Breath taking view of the Golf Course and water with nature sounds...

2 Bedrooms
2 Bathrooms
$116 / night (excl. fees & taxes)
Icon
Icon
Tropical Beach Condo!
Icon

Peaceful and Serene

1 Bedroom
1 Bathroom
5IconIconIconIconIcon
11 reviews
$275 - $300 / night (excl. fees & taxes)
Icon
Icon
Icon
Craig House with Heated Pool
Icon

Craig House with Heated Pool

2 Bedrooms
2 Bathrooms
4.8IconIconIconIconIcon
107 reviews
$148 - $190 / night (excl. fees & taxes)
Icon
Icon
Golf Course and Private Pool Views
Icon

For the Ultimate Vacation Come Stay at Rosedale Golf & Country Club!!

2 Bedrooms
2 Bathrooms
$225 / night (excl. fees & taxes)
Icon
Icon
Condo 6 miles from breathtaking Anna Maria Island
Icon

2 bedroom, 2 bath, sleeps 6. Under 6 miles from the breathtaking Anna Maria Island beaches

2 Bedrooms
2 Bathrooms
$67 / night (excl. fees & taxes)
Icon
Icon
Welcome to Paradise
Icon

6 miles from Anna Maria Island Beaches

3 Bedrooms
2 Bathrooms
$170 / night (excl. fees & taxes)
Icon
Icon
Bradenton Boho Bungalow
Icon

NO CLEANING FEE-Heated Pool-Completely Remodeled-King Beds-Close to IMG, restaurants & beaches-2GB Fiber Internet-10% off 7+ nights

3 Bedrooms
2 Bathrooms
$300 - $375 / night (excl. fees & taxes)
Icon
Icon
Icon
Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub
Icon

Mins to Anna Maria Beaches! Saltwater Pool/Hot Tub

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
50 reviews
$500 - $700 / night (excl. fees & taxes)
Icon
Icon
Icon
The Surof House
Icon

Anna Maria Island Direct Beach/ Gulf Views

2 Bedrooms
1 Bathroom
$480 - $1035 / night (excl. fees & taxes)
Icon
Icon
New! Salt Pool + Hot Tub + Anna Maria Beaches!
Icon

New! Salt Pool + Hot Tub + Anna Maria Beaches!

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
3 reviews
$300 - $525 / night (excl. fees & taxes)
Icon
Icon
Palm Paradise
Icon

Palm Paradise

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
3 reviews
$220 / night (excl. fees & taxes)
Icon
Icon
Sunny Retreat Near AMI, IMG, Beaches-Pet Friendly
Icon

Sunny Retreat Near AMI Beaches & Manatee River - Pet Friendly

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
15 reviews
$225 / night (excl. fees & taxes)
Icon
Icon
Icon
Making Waves
Icon

Heated Pool/Walk to Anna Maria Beaches/Restaurants

3 Bedrooms
3 Bathrooms
$700 - $1100 / night (excl. fees & taxes)
Icon
Icon
Poolside paradise
Icon

Poolside paradise Your family oasis

5 Bedrooms
4 Bathrooms
4.81IconIconIconIconIcon
21 reviews
$599 / night (excl. fees & taxes)
Icon
Icon
Cozy Outdoor Livingl+Private Yard+AMI in 5 Miles!
Icon

Prime location+Private HTD Saltwater Pool+Spacious Master Suite w/private pool access. New Furniture, Appliances, Quartz Countertops, Travertine Patio

4 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
33 reviews
$234 - $799 / night (excl. fees & taxes)
Icon
Icon
Icon
The River House
Icon

Relaxing Riverhouse - free parking pass in Pass A Grille beach- 30 min. drive

4 Bedrooms
3 Bathrooms
5IconIconIconIconIcon
3 reviews
$500 / night (excl. fees & taxes)
Icon
Icon
Gulf Coast Paradise Hideaway
Icon

Gulf Coast Paradise Hideaway

1 Bedroom
1 Bathroom
$95 / night (excl. fees & taxes)
Icon
Icon
Icon
Florida Pool Villa Happy Gator
Icon

10 Minutes to the Beach! Heated Pool with ♥SUNSHELF♥SW exposure♥

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
102 reviews
$200 - $270 / night (excl. fees & taxes)
Icon
Icon
Icon
First Responder•Displaced Home Owners•Pool/Hot Tub
Icon

⁕New! 4 BR, Heated Pool/Hot Tub, Arcade/15 MIN Anna Maria Island Beach

4 Bedrooms
2 Bathrooms
4.8IconIconIconIconIcon
15 reviews
$173 - $1335 / night (excl. fees & taxes)
    21 – 40 Rentals