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3,437 Houses

(5) Very Good 

Certificate of Excellence

30

SAILPORT-Tampa Bay FL - Waterfront Vacation Condo

Tampa / Tampa Bay

Tampa condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

Certificate of Excellence

Price per night from

$134

Responds fast!
avg. 39 minutes

Price per night from

$134

Great rentals within 20 miles that match your search

Distance approx 16.13 km from Tampa Bay

25

2 Bedroom Beachfront Home on Siesta Beach!! Directly on the beach!! 47 Beach Rd

Florida / Siesta Key

Siesta Key townhouse

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$456

Price per night from

$456

Distance approx 3.93 km from Tampa Bay

(6) Excellent 

16

Cut House- Waterfront, dock, ocean access, beach

Florida / Palmetto

Palmetto house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
“delightful” Three 60+ hockey players and their wives in search of a house close to the Ellenton Ice arena arrived here in april not knowing what to anticipate. We were delighted to find the accommodations exceptionally charming and clean. The views o
…see more

Price per night from

$286

Price per night from

$286

Distance approx 18.04 km from Tampa Bay

(23) Very Good 

40

Sandy Toes Siesta Key Florida (6796)

Florida / Siesta Key

Siesta Key house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Fantastic!!!” Loved it!!! This place was very clean, close enough to beach, very spacious, tastefully decorated with upgrades, decent pool, a manager on site, and more beach gear than you could ask for. ...Chairs, games, rafts, umbrellas, bikes, towe
…see more

Price per night from

$457

Responds fast!
avg. 56 minutes

Price per night from

$457

Distance approx 9.67 km from Tampa Bay

(22) Very Good 

42

Steps to Beach, Gulf View, Footprints in the Sand

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly
“Footprints in the sand” We had a great time on Anna Maria Island. Footprints in the sand,its closeness to the beaches,restaurants and shops made it very convenient.The place was well stocked with all basic needs & amenities that were listed. Thanks
…see more

Price per night from

$147

Responds fast!
avg. 1 hour 51 minutes

Price per night from

$147

Distance approx 10.98 km from Tampa Bay

5

Two Story Condo on the Gulf of Mexico

Florida / Longboat Key

Longboat Key condo

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$540

Price per night from

$540

Distance approx 9.75 km from Tampa Bay

15

Private Bungalow on Canal a block from Beach

Florida / Longboat Key

Longboat Key house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$164

Responds fast!
avg. 1 hour 34 minutes

Price per night from

$164

Distance approx 10.31 km from Tampa Bay

(4) Excellent 

15

Shady Palms - Real Beachfront on the Gulf of Mexico

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Old Florida Charm” This home had all the beauty and grace of Old Florida! It was well furnished with amenities plus delightful treasures of decor.The view of the Gulf was outstanding from many windows throughout the house as well as from the shady ba
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Price per night from

$394

Price per night from

$394

Distance approx 18.08 km from Tampa Bay

(2) Excellent 

43

8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (2)

Florida / Siesta Key

Siesta Key house

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Child Friendly

Price per night from

$128

Responds fast!
avg. 1 hour 0 minutes

Price per night from

$128

Distance approx 10.85 km from Tampa Bay

(5) Very Good 

23

Coconuts Two Bedroom 118 Upstairs Courtyard

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$179

Responds fast!
avg. 3 hours 50 minutes

Price per night from

$179

Distance approx 17.17 km from Tampa Bay

53

Crescent Beach Rental on Siesta Key, Sarasota, FL

Southwest Gulf Coast / Sarasota

Sarasota condo

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$138

Price per night from

$138

Distance approx 9.66 km from Tampa Bay

(4) Excellent 

17

Two bedroom condo across street from Gulf of Mexico, Bradenton Beach, Fl

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$160

Responds fast!
avg. 2 hours 18 minutes

Price per night from

$160

Distance approx 7.81 km from Tampa Bay

(4) Excellent 

19

Paradise Found "II"

Southwest Gulf Coast / Bradenton

Bradenton apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$137

Responds fast!
avg. 3 hours 3 minutes

Price per night from

$137

Distance approx 10.42 km from Tampa Bay

(14) Excellent 

28

Anna Maria Great Townhouse, Great Value!

Anna Maria Island / Holmes Beach

Holmes Beach house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“Famous Holiday” Everything was so perfekt ... WE CAME back next Year THE HOUSE BEAUTIFUL AND CLEAN.. THE Area perfekt
…see more

Price per night from

$206

Responds fast!
avg. 3 hours 13 minutes

Price per night from

$206

Distance approx 5.54 km from Tampa Bay

12

Barb's BaySide Retreat

Florida / Palma Sola

Palma Sola house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$165

Price per night from

$165

Distance approx 18.15 km from Tampa Bay

24

NEW! Siesta Key Condo - Steps to Crescent Beach!

Florida / Gulf Gate Branch

Gulf Gate Branch condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$257

Responds fast!
avg. 26 minutes

Price per night from

$257

Distance approx 10.77 km from Tampa Bay

(2) Excellent 

23

Tiffany Place - Gulf Front Complex

Anna Maria Island / Holmes Beach

Holmes Beach condo

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$206

Price per night from

$206

Distance approx 16.58 km from Tampa Bay

22

ISLAND REEF CONDO - BEAUTIFUL END UNIT - SMALL PET WELCOME

Florida / Siesta Key

Siesta Key condo

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Swimming pool
  • Air conditioning
  • Pet Friendly

Price per night from

$248

Price per night from

$248

Distance approx 4.76 km from Tampa Bay

(3)  

20

Country Club Veranda

Southwest Gulf Coast / Bradenton

Bradenton condo

2 5 21 nights min

  • 2 bedrooms
  • sleeps 5
  • 21 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$64

Price per night from

$64

Distance approx 6.63 km from Tampa Bay

8

Waterfront Ducks Unlimited Bunkhouse

Florida / Braden River

Braden River cottage

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 11 mi
  • Child Friendly
  • Air conditioning

Price per night from

$52

Price per night from

$52

Distance approx 17.09 km from Tampa Bay

5

Beautiful Condo overlooking Intercoastal Waterway

Florida / Siesta Key

Siesta Key house

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$153

Price per night from

$153

Distance approx 6.63 km from Tampa Bay

9

Waterfront Glamping Sarasota Steampunk Style Cabin

Florida / Braden River

Braden River cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 11 mi
  • Child Friendly
  • Air conditioning

Price per night from

$52

Price per night from

$52

Distance approx 10.79 km from Tampa Bay

24

Seagull Way

Anna Maria Island / Anna Maria

Anna Maria house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Car not necessary

Price per night from

$369

Responds fast!
avg. 3 hours 24 minutes

Price per night from

$369

Distance approx 12.81 km from Tampa Bay

25

LUXURY WATERFRONT PROPERY

Sarasota / Lido Key

Lido Key house

5 10 30 nights min

  • 5 bedrooms
  • sleeps 10
  • 30 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$952

Price per night from

$952

Distance approx 9.73 km from Tampa Bay

15

2501 Gulf Drive Unit 202

Florida / Cortez

Cortez house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Car not necessary

Price per night from

$159

Responds fast!
avg. 3 hours 28 minutes

Price per night from

$159

Distance approx 10.83 km from Tampa Bay

10

Direct Beachfront on Serene Gulf of Mexico, Amazing View, Family Friendly

Florida / Longboat Key

Longboat Key villa

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$481

Price per night from

$481

Distance approx 16.81 km from Tampa Bay

20

Tropical Dreams Sarasota -Updated, Near Siesta Key, Lg patio King beds Unit #2

Southwest Gulf Coast / Sarasota

Sarasota apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$147

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$147

Distance approx 4.94 km from Tampa Bay

26

The Waterview Private Pool, Hot Tub, Games Room

Southwest Gulf Coast / Bradenton

Bradenton house

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$157

Price per night from

$157

Distance approx 19.57 km from Tampa Bay

(2) Excellent 

9

Desirable location near downtown St. Petersburg

Florida / St. Petersburg

St. Petersburg condo

1 2 30 nights min

  • 1 bedroom
  • sleeps 2
  • 30 nights min
  • Ask about children
  • Air conditioning

Price per night from

$32

Price per night from

$32

Distance approx 16.63 km from Tampa Bay

(1) Excellent 

18

Beautiful & Modern Condo - Walk to Beach & Village

Florida / Siesta Key

Siesta Key condo

2 6 14 nights min

  • 2 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool

Price per night from

$123

Price per night from

$123

Distance approx 16.15 km from Tampa Bay

(3) Excellent 

41

2 BR, 2 Bath, Siesta Key Village Condo with Pool

Florida / Siesta Key

Siesta Key condo

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$144

Price per night from

$144

Distance approx 17.44 km from Tampa Bay

19

W22-Cozy St Pete Beach House 2nd Fl w/WiFi&Bikes

Florida / St. Pete Beach

St. Pete Beach house

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 1 mi
  • Child Friendly
  • Car not necessary

Price per night from

$164

Price per night from

$164

Distance approx 14.33 km from Tampa Bay

31

Siesta Dream House- 4 BR, 3.5 BA Villa W/ Heated Pool, Spa On Siesta Key

Florida / Siesta Key

Siesta Key house

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$325

Price per night from

$325

Distance approx 11.74 km from Tampa Bay

55

Serendipity Trois - 4 bedroom 4 & 1/2 bath w/pool

Anna Maria Island / Anna Maria

Anna Maria house

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$688

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$688

Distance approx 15.65 km from Tampa Bay

(5) Very Good 

33

Tampa Bay 3b/3b Townhouse, Private Beach Community U-3232

Florida / Ruskin

Ruskin townhouse

3 9 min stay varies

  • 3 bedrooms
  • sleeps 9
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Price per night from

$217

Responds fast!
avg. 2 hours 0 minutes

Price per night from

$217

Distance approx 18.07 km from Tampa Bay

31

Casa Coquina – 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach

Florida / Siesta Key

Siesta Key house

4 14 7 nights min

  • 4 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$396

Price per night from

$396

Distance approx 8.97 km from Tampa Bay

(7) Very Good 

15

Braden River Bayou Studio & CottageSarasota/Bradenton FL

Southwest Gulf Coast / Bradenton

Bradenton apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 mi
  • Air conditioning

Price per night from

$143

Responds fast!
avg. 2 hours 15 minutes

Price per night from

$143

Distance approx 18.07 km from Tampa Bay

38

Casa Eulimia – 4BR/3BA Private Home, Heated Pool, Private Cabana, Walk to Beach

Florida / Siesta Key

Siesta Key house

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$394

Price per night from

$394