Longboat Key Vacation Rentals
Poolside paradise Your family oasis
5 Bedrooms
4 Bathrooms
4.81
21 reviews$599 / night (excl. fees & taxes)
Anna Maria Island - 3Bed 2Bath Home - Private Heated Pool - Walk to Beach
3 Bedrooms
2 Bathrooms
5
49 reviews$450 / night (excl. fees & taxes)
Coconuts included!+Family Friendly!+Close to Beach
2 Bedrooms
2 Bathrooms
5
1 review$190 - $450 / night (excl. fees & taxes)
Loggerhead - AMI Oasis w/ Private Pool
2 Bedrooms
2 Bathrooms
5
13 reviews$210 - $550 / night (excl. fees & taxes)
Craig House with Heated Pool
2 Bedrooms
2 Bathrooms
4.8
107 reviews$148 - $179 / night (excl. fees & taxes)
Gorgeous Beach Home with heated pool
3 Bedrooms
3 Bathrooms
5
2 reviews$300 - $450 / night (excl. fees & taxes)
Art Deco/Mid-Century Modern Masterpiece in the Heart of Downtown--Across from the Marina! Multi-Month High Season Only
2 Bedrooms
2 Bathrooms
$259 / night (excl. fees & taxes)
Gulf Coast Paradise Hideaway
1 Bedroom
1 Bathroom
$95 / 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
4.9
20 reviews$128 - $378 / 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
3 Bathrooms
5
43 reviews$198 - $521 / 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
3 Bathrooms
5
28 reviews$198 - $507 / 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$124 - $378 / night (excl. fees & taxes)
Downtown Compound |Pet Friendly | Families |Groups
8 Bedrooms
9 Bathrooms
$941 - $2970 / 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 / night (excl. fees & taxes)
(3) E-Z Payments, beach supply & more
2 Bedrooms
2 Bathrooms
4.57
49 reviews$225 / night (excl. fees & taxes)
Tropical Oasis Heated Pool Hot Tub Near Siesta Key
2 Bedrooms
2 Bathrooms
5
90 reviews$202 - $580 / 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)
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