Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 1
Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 2
Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 3
Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 4
Waterfront 2/1 Apt in heart of Palm Harbor/Ozona image 5

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona

2 bedrooms·1 bath
Palm Harbor • Florida
4.85(62 reviews)

$1,195.00 USD total for 4 nights

Oct 19 – 23, 2026

3 bed/2 bath Home W/ Gulf Water Access image 1
3 bed/2 bath Home W/ Gulf Water Access image 2
3 bed/2 bath Home W/ Gulf Water Access image 3
3 bed/2 bath Home W/ Gulf Water Access image 4
3 bed/2 bath Home W/ Gulf Water Access image 5

3 bed/2 bath Home W/ Gulf Water Access

3 bedrooms·2 baths
Palm Harbor • Florida
4.74(50 reviews)

$1,450.00 USD total for 5 nights

Mar 26 – 31, 2027

Treasure Island Waterfront Luxury Condo image 5
Treasure Island Waterfront Luxury Condo image 1
Treasure Island Waterfront Luxury Condo image 2
Treasure Island Waterfront Luxury Condo image 3
Treasure Island Waterfront Luxury Condo image 4

Treasure Island Waterfront Luxury Condo

2 bedrooms·2 baths
Treasure Island • Florida
5(3 reviews)

$2,202.00 USD total for 6 nights

Oct 27 – Nov 2, 2026

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 1
Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 2
Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 3
Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 4
Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber image 5

Waterfront 2/1 Apt. Ozona/Palm Harbor (Beachcomber

2 bedrooms·1 bath
Palm Harbor • Florida
4.86(74 reviews)

$762.00 USD total for 3 nights

Oct 19 – 22, 2026

cozy living room
modern kitchen
modern bedroom
coffee station
front door

Seashell Studio sanctuary by the sea

1 bedroom·1 bath
St. Petersburg • Florida
Coastal Cottage Near Beaches w/ Golf Cart Rental! image 1
Rent our Golf Cart, "Bolt" !
Coastal Cottage Near Beaches w/ Golf Cart Rental! image 3
Coastal Cottage Near Beaches w/ Golf Cart Rental! image 4
Master Suite

Coastal Cottage Near Beaches w/ Golf Cart Rental!

2 bedrooms·2 baths
Palm Harbor • Florida
4.99(71 reviews)

$759.00 USD total for 3 nights

Oct 19 – 22, 2026

The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage
The Bayou Breeze Cottage

The Bayou Breeze Cottage

1 bedroom·1 bath
St. Petersburg • Florida
5(28 reviews)

$415.61 USD $348.49 USD total for 3 nights

Oct 19 – 22, 2026

The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage
The Coffee Pot Cottage

The Coffee Pot Cottage

2 bedrooms·1 bath
St. Petersburg • Florida
5(26 reviews)

$636.75 USD $529.40 USD total for 3 nights

Oct 24 – 27, 2026

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +
Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +
Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +
Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +
Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

Pvt Pool, Free Kayaks, Steps to Gulf, Fish, Bike Trail +

1 bedroom·1 bath
Dunedin • Florida
5(93 reviews)

$480.03 USD total for 3 nights

Oct 29 – Nov 1, 2026

Sit back and enjoy this beautiful coastal home where u can relax and enjoy what Florida can offer.
Pool home minutes from the beach. image 2
Pool home minutes from the beach. image 12
Pool home minutes from the beach. image 14
Pool home minutes from the beach. image 4

Pool home minutes from the beach.

3 bedrooms·2 baths
Palm Harbor • Florida
5(33 reviews)

$950.00 USD total for 3 nights

Oct 20 – 23, 2026

Modern Cozy Spot. Near Beach & DT. Yard & Parking image 1
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 2
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 3
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 4
Modern Cozy Spot. Near Beach & DT. Yard & Parking image 5

Adorable Studio East, close to beaches & downtown

0 bedrooms·1 bath
St. Petersburg • Florida
4.88(41 reviews)

$2,881.44 USD $2,214.83 USD total for 28 nights

Oct 22 – Nov 19, 2026

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill
Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill
Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill
Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill
Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

Private 2bdrm Suite/Kitchen/Laundry/Sunroom/Grill

2 bedrooms·1 bath
St. Petersburg • Florida
5(4 reviews)

$750.00 USD total for 5 nights

Oct 19 – 24, 2026

Exterior view of Studio East & Studio West. Each studio has private entrance and private yard, connected with a gate.
Studio 1 (East) private porch
Studio 1 (East) private porch and outdoor
Studio 1 (East)
Studio 1 (East)

Adorable Pair - 2 private modern studios

2 bedrooms·2 baths
St. Petersburg • Florida
4.5(2 reviews)

$6,282.04 USD total for 28 nights

Nov 3 – Dec 1, 2026

Studio w/ yard & parking, near beach & downtown. image 1
Studio w/ yard & parking, near beach & downtown. image 2
Studio w/ yard & parking, near beach & downtown. image 3
Studio w/ yard & parking, near beach & downtown. image 4
Studio w/ yard & parking, near beach & downtown. image 5

Adorable Studio West, close to beaches & downtown

0 bedrooms·1 bath
St. Petersburg • Florida
4.72(50 reviews)

$2,881.44 USD $2,348.15 USD total for 28 nights

Nov 3 – Dec 1, 2026

Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown
Adorable Private Cottage close to beach & downtown

Adorable Private Cottage close to beach & downtown

2 bedrooms·1 bath
St. Petersburg • Florida
5(268 reviews)
$139 – $1,999/ night(excl. fees & taxes)
Holiday Family Retreat. 4BR/3BA + Private Suites
Living room
Holiday Family Retreat. 4BR/3BA + Private Suites
Holiday Family Retreat. 4BR/3BA + Private Suites
Holiday Family Retreat. 4BR/3BA + Private Suites

Holiday Family Retreat. 4BR/3BA + Private Suites

4 bedrooms·3 baths
St. Petersburg • Florida
$399/ night(excl. fees & taxes)
Private Guest suite/Patio/Laundry/Parking/Beach
Private Guest suite/Patio/Laundry/Parking/Beach
Private Guest suite/Patio/Laundry/Parking/Beach
Private Guest suite/Patio/Laundry/Parking/Beach
Private Guest suite/Patio/Laundry/Parking/Beach

Private Guest suite/Patio/Laundry/Parking/Beach

1 bedroom·1 bath
St. Petersburg • Florida
4.46(13 reviews)

$625.00 USD total for 7 nights

Oct 19 – 26, 2026

Flamingo House Tropical Oasis Bike Trail Tennis ct
Flamingo House Tropical Oasis Bike Trail Tennis ct
Flamingo House Tropical Oasis Bike Trail Tennis ct
Flamingo House Tropical Oasis Bike Trail Tennis ct
Flamingo House Tropical Oasis Bike Trail Tennis ct

Flamingo House Tropical Oasis Bike Trail Tennis ct

3 bedrooms·1 bath
St. Petersburg • Florida
4.63(19 reviews)

$3,949.00 USD total for 30 nights

Oct 19 – Nov 18, 2026

Private tropical pool oasis with loungers, shade, and resort-style vibes
Tropical-inspired bedroom with en suite bath and stylish barn door
Private pool deck with lounge chairs, pool noodles, and floats included. Fully fenced, tropical landscaping, sleeps 10. Gulfport/South St. Pete, FL.
Private tropical pool oasis with loungers, shade, and lush palms
Open-plan living and kitchen — 65-inch smart TV, breakfast bar with 4 stools, and mustard yellow sofas. 4-bedroom vacation rental, St. Petersburg, FL.

Tropical Disco 70s Disco Lounge and Heated Pool Near St Pete Beach

4 bedrooms·2 baths
St. Petersburg • Florida
5(187 reviews)

$1,214.13 USD total for 3 nights

Nov 9 – 12, 2026

Sunset Walks on Sunset Beach
Sunset Walks on Sunset Beach
Sunset Walks on Sunset Beach
Sunset Walks on Sunset Beach
Sunset Walks on Sunset Beach

Sunset Walks on Sunset Beach

3 bedrooms·3 baths
Treasure Island • Florida
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!
FREE NIGHT! Jeffreys Bay African retreat!

FREE NIGHT! Jeffreys Bay African retreat!

2 bedrooms·1 bath
Treasure Island • Florida

$676.10 USD total for 3 nights

Apr 22 – 25, 2027

FREE NIGHT! Aloha! Hawaiian surf inspired retreat
FREE NIGHT! Aloha! Hawaiian surf inspired retreat
FREE NIGHT! Aloha! Hawaiian surf inspired retreat
FREE NIGHT! Aloha! Hawaiian surf inspired retreat
FREE NIGHT! Aloha! Hawaiian surf inspired retreat

FREE NIGHT! Aloha! Hawaiian surf inspired retreat

1 bedroom·2 baths
Treasure Island • Florida

$609.40 USD total for 3 nights

Apr 22 – 25, 2027

Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!
Funshine Sunset Beach - Steps from the beach!!

Funshine Sunset Beach - Steps from the beach!!

1 bedroom·1 bath
Treasure Island • Florida
5(142 reviews)

$881.67 USD total for 3 nights

Oct 23 – 26, 2026

Seasonal Waterfront Vacation Condo
Seasonal Waterfront Vacation Condo
Seasonal Waterfront Vacation Condo
Seasonal Waterfront Vacation Condo
Seasonal Waterfront Vacation Condo

Seasonal Waterfront Vacation Condo

1 bedroom·1 bath
South Pasadena • Florida

$3,150.00 USD total for 30 nights

Mar 26 – Apr 25, 2027