Holiday rentals near The Upper Tampa Bay Trail
We found 10,826 holiday rentals — enter your dates for availability
Take a look at holiday rentals close to The Upper Tampa Bay Trail that can be your home away from home. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you expect for your stay, which might include air conditioning and a pool. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - The Upper Tampa Bay Trail
Showing deals for:26 Sept - 3 Oct
Image gallery for BBQ Games, King Beds, Private Yard
9.09.0 out of 10 rating
Wonderful
(9 reviews)
BBQ Games, King Beds, Private Yard
Seminole, FL
7% off
Price is NZ$2,714
NZ$2,714
NZ$388 per night
includes taxes & fees
Image gallery for Bay Breeze Retreat +15 minutes from central TPA
9.29.2 out of 10 rating
Wonderful
(20 reviews)
Bay Breeze Retreat +15 minutes from central TPA
Tampa, FL
7% off
Price is NZ$2,385
NZ$2,385
NZ$341 per night
includes taxes & fees
Image gallery for 84’YACHT, DEEP SPRING DISCOUNTS,KING BEDS,MASSAGES,CHEF,KAYAKS,SUP
9.89.8 out of 10 rating
Exceptional
(63 reviews)
84’YACHT, DEEP SPRING DISCOUNTS,KING BEDS,MASSAGES,CHEF,KAYAKS,SUP
St. Petersburg, FL
8% off
Price is NZ$5,124
NZ$5,124
NZ$732 per night
includes taxes & fees
Image gallery for Dogs Welcome| 2BD/2BA Pool Home| Near BEACH| Location
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Dogs Welcome| 2BD/2BA Pool Home| Near BEACH| Location
Largo, FL
10% off
Price is NZ$3,304
NZ$3,304
NZ$472 per night
includes taxes & fees
Image gallery for 2 Miles to Beach! Firepit ~ Heated Pool ~ PuttPutt
9.89.8 out of 10 rating
Exceptional
(14 reviews)
2 Miles to Beach! Firepit ~ Heated Pool ~ PuttPutt
Largo, Florida
10% off
Price is NZ$5,157
NZ$5,157
NZ$737 per night
includes taxes & fees
Image gallery for Milos Beach House "BRAND NEW" A Luxe Haven Steps from the Beach-ROOFTOP SWIMMING
1010 out of 10 rating
Exceptional
(22 reviews)
Milos Beach House "BRAND NEW" A Luxe Haven Steps from the Beach-ROOFTOP SWIMMING
Indian Rocks Beach, FL
8% off
Price is NZ$29,918
NZ$29,918
NZ$4,274 per night
includes taxes & fees
Image gallery for Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!
1010 out of 10 rating
Exceptional
(73 reviews)
Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!
Tampa, FL
7% off
Price is NZ$1,905
NZ$1,905
NZ$272 per night
includes taxes & fees
Image gallery for Adorable Oasis - Pool + Arcade - Ace Location
9.09.0 out of 10 rating
Wonderful
(30 reviews)
Adorable Oasis - Pool + Arcade - Ace Location
Tampa, FL
7% off
Price is NZ$2,764
NZ$2,764
NZ$395 per night
includes taxes & fees
Image gallery for 2/2 cozy home mins from Downtown Tampa, Ybor City, Amalie Arena ,Bucs Stadium!
9.49.4 out of 10 rating
Exceptional
(56 reviews)
2/2 cozy home mins from Downtown Tampa, Ybor City, Amalie Arena ,Bucs Stadium!
Tampa, FL
7% off
Price is NZ$2,024
NZ$2,024
NZ$289 per night
includes taxes & fees
Image gallery for 2BR home near Madeira Beach, Florida
9.89.8 out of 10 rating
Exceptional
(11 reviews)
2BR home near Madeira Beach, Florida
St. Petersburg, FL
5% off
Price is NZ$1,850
NZ$1,850
NZ$264 per night
includes taxes & fees
Image gallery for Paradise Waterfront Resort! Pool &Spa with swim-up bar, Dock Kayaks, Pet Welcome
9.69.6 out of 10 rating
Exceptional
(75 reviews)
Paradise Waterfront Resort! Pool &Spa with swim-up bar, Dock Kayaks, Pet Welcome
Apollo Beach, FL
8% off
Price is NZ$6,246
NZ$6,246
NZ$892 per night
includes taxes & fees
Image gallery for The Graystone - Family Home|Hot Tub|Play Set
9.69.6 out of 10 rating
Exceptional
(5 reviews)
The Graystone - Family Home|Hot Tub|Play Set
Tampa, Florida
7% off
Price is NZ$3,671
NZ$3,671
NZ$524 per night
includes taxes & fees
Image gallery for Flamingo Hideaway - Chic Pool Home 3min to Beach!
1010 out of 10 rating
Exceptional
(17 reviews)
Flamingo Hideaway - Chic Pool Home 3min to Beach!
Seminole, FL
8% off
Price is NZ$3,776
NZ$3,776
NZ$539 per night
includes taxes & fees
Image gallery for NEW Fully renovated Gulf front home w/private resort style pool, outdoor kitchen
1010 out of 10 rating
Exceptional
(38 reviews)
NEW Fully renovated Gulf front home w/private resort style pool, outdoor kitchen
Crystal Beach, FL
8% off
Price is NZ$12,338
NZ$12,338
NZ$1,763 per night
includes taxes & fees
Image gallery for Beachside Escape~Pool~Golf Sim~GameRoom~Volleyball
8.88.8 out of 10 rating
Excellent
(5 reviews)
Beachside Escape~Pool~Golf Sim~GameRoom~Volleyball
Seminole, Florida
7% off
Price is NZ$7,386
NZ$7,386
NZ$1,055 per night
includes taxes & fees
Image gallery for PRIVATE ESTATE BY BEACH 5BR 3BA 2 king masters, heated pooL, hottub, by beach.
9.89.8 out of 10 rating
Exceptional
(34 reviews)
PRIVATE ESTATE BY BEACH 5BR 3BA 2 king masters, heated pooL, hottub, by beach.
Seminole, FL
28% off
Price is NZ$5,157
NZ$5,157
NZ$737 per night
includes taxes & fees
Image gallery for Spacious Family Waterfront Beach Home with Pool
9.89.8 out of 10 rating
Exceptional
(20 reviews)
Spacious Family Waterfront Beach Home with Pool
Indian Rocks Beach, FL
8% off
Price is NZ$14,198
NZ$14,198
NZ$2,028 per night
includes taxes & fees
Image gallery for A Piece of History, Great Babe Ruth’s Build!! - Spanish Style Hacienda, 4BR/5BA!
1010 out of 10 rating
Exceptional
(27 reviews)
A Piece of History, Great Babe Ruth’s Build!! - Spanish Style Hacienda, 4BR/5BA!
St. Petersburg, FL
8% off
Price is NZ$10,717
NZ$10,717
NZ$1,531 per night
includes taxes & fees
Image gallery for Beautiful 3 bedroom private waterfront 511 Harbor Home in Indian Rocks Beach POOL+Hot TUB
1010 out of 10 rating
Exceptional
(27 reviews)
Beautiful 3 bedroom private waterfront 511 Harbor Home in Indian Rocks Beach POOL+Hot TUB
Indian Rocks Beach, FL
7% off
Price is NZ$8,288
NZ$8,288
NZ$1,184 per night
includes taxes & fees
Image gallery for Lake living with beautiful views!
1010 out of 10 rating
Exceptional
(99 reviews)
Lake living with beautiful views!
Land O' Lakes, FL
8% off
Price is NZ$2,190
NZ$2,190
NZ$313 per night
includes taxes & fees
Image gallery for Near Clearwater Beach - Pool Home Retreat
1010 out of 10 rating
Exceptional
(24 reviews)
Near Clearwater Beach - Pool Home Retreat
Clearwater, FL
8% off
Price is NZ$5,173
NZ$5,173
NZ$739 per night
includes taxes & fees
Image gallery for A Little Slice of Key West on Lake Tarpon - Kayak and fish from the back yard
1010 out of 10 rating
Exceptional
(42 reviews)
A Little Slice of Key West on Lake Tarpon - Kayak and fish from the back yard
Palm Harbor, FL
7% off
Price is NZ$2,685
NZ$2,685
NZ$384 per night
includes taxes & fees
Image gallery for Shady Oaks Estate near Tampa
1010 out of 10 rating
Exceptional
(16 reviews)
Shady Oaks Estate near Tampa
Brandon, FL
11% off
Price is NZ$3,067
NZ$3,067
NZ$438 per night
includes taxes & fees
Image gallery for Golf&Sea Luxurious vacation home W/Pool, Spa @High-end neighborhood Pet-Friendly
9.49.4 out of 10 rating
Exceptional
(56 reviews)
Golf&Sea Luxurious vacation home W/Pool, Spa @High-end neighborhood Pet-Friendly
Apollo Beach, FL
8% off
Price is NZ$6,246
NZ$6,246
NZ$892 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Upper Tampa Bay Trail
Beach Vacation! Near Clearwater Beach, Pool, Bar, Free Buffet Breakfast
Sleeps 4 · 1 bedroom · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
194 reviews(194 reviews)
Sunset Vistas Two Bedroom Beachfront Suites
Sleeps 6 · 1 bathroom
8.88.8 out of 10
Excellentexcellent
3,248 reviews(3,248 reviews)
New Beachfront Property in Exclusive Resort
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
184 reviews(184 reviews)
Provident Oceana Beachfront Suites
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
568 reviews(568 reviews)
Look No More! Outdoor Pool, On-Site Bar, Short Walk From Clearwater Beach
Sleeps 3 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
75 reviews(75 reviews)
John's Pass Hotel
Sleeps 8 · 3 bedrooms
8.48.4 out of 10
Very goodvery good
199 reviews(199 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value