Longboat Key Vacation Rentals
Amazing NEW saltwater pool/spa close to AMI & IMG!
3 Bedrooms
2 Bathrooms
5
36 reviews$323 - $900 / night
(excl. fees & taxes)
Updated two stories home with private pool, pool table, ping pong table and games. Only 5 miles to Anna Maria Island and 23 miles to Siesta Key.
4 Bedrooms
3 Bathrooms
5
22 reviews$399 - $629 / night
(excl. fees & taxes)
Poolside paradise LillyBug Lane LLC
5 Bedrooms
4 Bathrooms
4.89
9 reviews$300 - $650 / night
(excl. fees & taxes)
Anna Maria Island - 3Bed 2Bath Home - Private Heated Pool - Walk to Beach
3 Bedrooms
2 Bathrooms
5
49 reviews$500 / night
(excl. fees & taxes)
Coconuts included!+Family Friendly!+Close to Beach
2 Bedrooms
2 Bathrooms
5
1 review$200 - $450 / night
(excl. fees & taxes)
Loggerhead - AMI Oasis w/ Private Pool
2 Bedrooms
2 Bathrooms
$213 - $550 / night
(excl. fees & taxes)
Craig House with Heated Pool
2 Bedrooms
2 Bathrooms
4.8
105 reviews$155 - $198 / night
(excl. fees & taxes)
Gorgeous Beach Home with heated pool
3 Bedrooms
3 Bathrooms
5
2 reviews$300 - $500 / night
(excl. fees & taxes)
Beach Downtown Pet-friendly 1 Bedroom Apartment at 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground, and two dog parks.
1 Bedroom
1 Bathroom
4.89
19 reviews$95 - $289 / night
(excl. fees & taxes)
Beach Downtown Pet-friendly 1 Bedroom Apartment at 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground, and two dog parks.
1 Bedroom
1 Bathroom
5
7 reviews$95 - $288 / night
(excl. fees & taxes)
Beach-town Pet-Friendly Downtown Sarasota Home @ 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground & two dog parks.
3 Bedrooms
3½ Bathrooms
5
28 reviews$213 - $508 / night
(excl. fees & taxes)
Beach Downtown Sarasota Pet-friendly Home @ 10 acre Gillespie Park with tennis, pickle ball & basketball courts, playground & two dog parks.
3 Bedrooms
3½ Bathrooms
5
22 reviews$213 - $508 / night
(excl. fees & taxes)
Real Florida Up Close!
3 Bedrooms
2 Bathrooms
$135 - $274 / night
(excl. fees & taxes)
Breath taking view of the Golf Course and water with nature sounds...
2 Bedrooms
2 Bathrooms
$116 / night
(excl. fees & taxes)
Relaxing Riverhouse - free parking pass in Pass A Grille beach- 30 min. drive
4 Bedrooms
3 Bathrooms
5
3 reviews$500 - $750 / night
(excl. fees & taxes)
(3) E-Z Payments, beach supply & more
2 Bedrooms
2 Bathrooms
4.57
49 reviews$225 - $235 / night
(excl. fees & taxes)
Tropical Oasis Heated Pool Hot Tub Near Siesta Key
2 Bedrooms
2 Bathrooms
5
64 reviews$234 - $575 / night
(excl. fees & taxes)
Come enjoy all of Sarasota and Siesta Key amenities without the congestion and just minutes to Siesta Key Beach.
2 Bedrooms
2 Bathrooms
$100 / night
(excl. fees & taxes)
For the Ultimate Vacation Come Stay at Rosedale Golf & Country Club!!
2 Bedrooms
2 Bathrooms
$225 / night
(excl. fees & taxes)
Casa Blanca Ranch Home near Siesta Key Beach
3 Bedrooms
2 Bathrooms
5
18 reviews$299 - $449 / night
(excl. fees & taxes)
Terms, Privacy, Currency & More
Save to Favorites
More filters
Beds & Baths
Bedrooms
0 +
Bathrooms
0 +More options
Pets
Managed by
Room Type
Property Type
Indoor Amenities
Outdoor Amenities
Languages