Holmes Beach Vacation Rentals

Icon
Featured
Icon
Beach, Bay, Food, Fun - 2BD/2BA
Icon

Beach, Bay, Food, Fun - 2BD/2BA

2 Bedrooms
2 Bathrooms
4.67IconIconIconIconIcon
9 reviews
$174 - $250 / night
(excl. fees & taxes)
Icon
Icon
Anna Maria Island - Azure Bliss Vacation Home
Icon

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

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
49 reviews
$500 / night
(excl. fees & taxes)
Icon
Icon
Making Waves
Icon

Heated Pool/Walk to Anna Maria Beaches/Restaurants

3 Bedrooms
3 Bathrooms
$603 - $900 / night
(excl. fees & taxes)
Icon
Icon
Gorgeous Beach Home with heated pool and dock
Icon

Gorgeous Beach Home with dock

3 Bedrooms
3 Bathrooms
$300 - $500 / night
(excl. fees & taxes)
Icon
Icon
Merry Mermaid Tree House
Icon

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

3 Bedrooms
3 Bathrooms
$1000 - $1300 / night
(excl. fees & taxes)
Icon
Icon
The Surof House
Icon

Anna Maria Island Direct Beach/ Gulf Views

2 Bedrooms
1 Bathroom
$500 - $1035 / night
(excl. fees & taxes)
Icon
Icon
2 Neighboring Homes with Pools! Close to AMI/IMG!
Icon

Rent 2 homes right next to each other! Perfect for multiple families and friends. Both homes are 3BR/2 bath with pools.

6 Bedrooms
4 Bathrooms
$798 - $1143 / night
(excl. fees & taxes)
Icon
Icon
Palma Rosa
Icon

Tropical pool home w/ outdoor TV & living space!

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
35 reviews
$241 - $854 / night
(excl. fees & taxes)
Icon
Icon
Palma Janoli
Icon

Amazing NEW saltwater pool/spa close to AMI & IMG!

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
36 reviews
$251 - $900 / night
(excl. fees & taxes)
Icon
Icon
Gulf Coast Home w/Private Pool  Near AMI & Beaches
Icon

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
5IconIconIconIconIcon
22 reviews
$399 - $579 / night
(excl. fees & taxes)
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
$400 - $575 / 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
12 reviews
$294 - $919 / night
(excl. fees & taxes)
Icon
Icon
Poolside paradise LillyBug Lane LLC
Icon

Poolside paradise LillyBug Lane LLC

5 Bedrooms
4 Bathrooms
4.89IconIconIconIconIcon
9 reviews
$275 - $650 / 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 - $365 / night
(excl. fees & taxes)
Icon
Icon
Icon
Craig House with Heated Pool
Icon

Craig House with Heated Pool

2 Bedrooms
2 Bathrooms
4.84IconIconIconIconIcon
83 reviews
$165 - $195 / 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 - $950 / night
(excl. fees & taxes)
Icon
Icon
Icon
Wind Swept Cottage
Icon

Beach Cottage above garage- Historic Pass-A-Grille-Private entrance

1 Bedroom
1 Bathroom
1 Guide
4.85IconIconIconIconIcon
27 reviews
$135 - $150 / night
(excl. fees & taxes)
Icon
Icon
Icon
Location-Quaint  Beach Front House-
Icon

Location-Quaint Beach Front House- Historic Pass a Grille-Steps to the beach.

2 Bedrooms
2 Bathrooms
1 Guide
4.99IconIconIconIconIcon
71 reviews
$500 - $700 / night
(excl. fees & taxes)
Icon
Icon
Tropical Escape Sarasota
Icon

Real Florida Up Close!

3 Bedrooms
2 Bathrooms
$135 - $274 / night
(excl. fees & taxes)
Icon
Icon
Icon
Beach Downtown Pet-friendly 1 BD @ The Park
Icon

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
4.86IconIconIconIconIcon
14 reviews
$95 - $267 / night
(excl. fees & taxes)
Icon
Icon
Icon
Beachtown Pet-Friendly Downtown Home @ The Park
Icon

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
5IconIconIconIconIcon
26 reviews
$213 - $468 / night
(excl. fees & taxes)
    1 – 20 Rentals