Villas with a pool Siesta Key | Apartments to rent with swimming facilities | Holiday Lettings

Close

Siesta Key

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

191 Holiday homes

Filters applied: Swimming pool

(2) Excellent 

26

Holiday villa in Siesta Key

Florida / Siesta Key

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £160 / night

£820 - £1520 / week

Book View

from £160 / night

(18) Excellent 

23

Siesta Key holiday condo rental

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.01 km
  • Swimming pool
“Awesome place! Comforts of home, but with an amazing view!!!” Loved our stay. Very comfortable beach getaway. Everything we needed was here. Great sunsets, beach, and pool. Saw two manatee, lots of pelican, and one turtle. The lanai overlooking the be
…see more

from £282 / night

£1969 / week

Book View

from £282 / night

(1) Excellent 

24

Home rental in Siesta Key with swimming pool

Florida / Siesta Key

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Swimming pool

from £152 / night

£1063 / week

Book View

from £152 / night

31

Holiday condo in Siesta Key

Florida / Siesta Key

2 5 14 nights min

  • 2 bedrooms
  • Sleeps 5
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £135 / night

£630 - £945 / week

Book View

from £135 / night

(1) Excellent 

18

Holiday condo in Siesta Key

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
“A hidden gem” Arrived 13th June 16 and stayed for an amazing 3 weeks. Minor problem re A/C sorted promptly by Nicole the owner next day after arrival and a mix of beers sent via courier by Nicole same day for minor inconvenience - very much appreciate
…see more

from £85 / night

£591 / week

Book View

from £85 / night

(6) Excellent 

20

Siesta Key holiday condo rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Perfect Gataway” My wife and I consider ourselves to be regulars at the Bay Tree. Diana Weiner has always made us feel special as we have celebrated many occasions over the years. The condo is a ture find and as the advert says it's luxury and spotl
…see more

Pricing unknown

Book View

Pricing unknown

(1) Excellent 

38

Holiday townhouse in Siesta Key

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £186 / night

£1024 - £1378 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £186 / night

22

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £304 / night

£2123 - £3786 / week

Enquire View

from £304 / night

25

Siesta Key holiday home rental

Florida / Siesta Key

6 12 6 nights min

  • 6 bedrooms
  • Sleeps 12
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £472 / night

£2749 - £3378 / week

Book View

from £472 / night

(5) Excellent 

24

Siesta Key holiday condo rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £169 / night

£1178 - £1760 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from £169 / night

33

Holiday villa rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £126 / night

£882 / week

Book View

Responds fast!
avg. 2 hours 50 minutes

from £126 / night

(5) Excellent 

29

Holiday condo in Siesta Key

Florida / Siesta Key

1 3 14 nights min

  • 1 bedroom
  • Sleeps 3
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £60 / night

£689 - £1182 / week

Book View

from £60 / night

(2) Excellent 

24

Holiday apartment in Siesta Key

Florida / Siesta Key

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool

from £209 / night

£1174 - £1650 / week

Book View

from £209 / night

(18) Very Good 

Certificate of Excellence

14

Siesta Key holiday apartment rental

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

Certificate of Excellence

from £71 / night

£493 - £847 / week

Book View

Responds fast!
avg. 2 hours 47 minutes

from £71 / night

(6) Excellent 

Certificate of Excellence

24

Holiday condo rental

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £124 / night

£867 - £1339 / week

Book View

Responds fast!
avg. 43 minutes

from £124 / night

25

Holiday condo rental

Florida / Siesta Key

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £71 / night

£497 / week

Book View

from £71 / night

(1) Excellent 

20

Holiday condo rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

from £126 / night

£882 - £1417 / week

Book View

from £126 / night

23

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £186 / night

£1300 - £2256 / week

Enquire View

from £186 / night

(12) Very Good 

31

Apartment rental in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £79 / night

£512 - £788 / week

Book View

Responds fast!
avg. 2 hours 9 minutes

from £79 / night

(1) Very Good 

32

Siesta Key holiday apartment rental

Florida / Siesta Key

2 5 14 nights min

  • 2 bedrooms
  • Sleeps 5
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £68 / night

£473 - £1032 / week

Book View

from £68 / night

38

Holiday apartment in Siesta Key

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £134 / night

£938 - £1560 / week

Enquire View

from £134 / night

(2) Excellent 

42

Holiday condo with swimming pool in Siesta Key

Florida / Siesta Key

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £71 / night

£491 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from £71 / night

36

Siesta Key holiday apartment rental

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £186 / night

£1300 - £2256 / week

Enquire View

from £186 / night

21

Holiday villa in Siesta Key

Florida / Siesta Key

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £96 / night

£667 / week

Book View

Responds fast!
avg. 2 hours 34 minutes

from £96 / night

(8) Excellent 

24

Condo rental in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £136 / night

£1028 - £1500 / week

Book View

Responds fast!
avg. 1 hour 49 minutes

from £136 / night

(5) Very Good 

Certificate of Excellence

42

Condo rental in Siesta Key

Florida / Siesta Key

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £124 / night

£863 - £1808 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £124 / night

(4) Very Good 

22

Siesta Key holiday villa rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £126 / night

£961 - £1418 / week

Book View

Responds fast!
avg. 1 hour 51 minutes

from £126 / night

(42) Excellent 

Certificate of Excellence

24

Holiday villa in Siesta Key

Florida / Siesta Key

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £96 / night

£630 - £1063 / week

Book View

Responds fast!
avg. 2 hours 1 minutes

from £96 / night

(1) Excellent 

29

Holiday home in Siesta Key

Florida / Siesta Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £197 / night

£1378 / week

Book View

Responds fast!
avg. 48 minutes

from £197 / night

15

Condo rental in Siesta Key with tennis court

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £90 / night

£630 - £788 / week

Book View

from £90 / night

(10) Excellent 

17

Holiday townhouse in Siesta Key

Florida / Siesta Key

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £212 / night

£1483 / week

Book View

from £212 / night

33

Holiday apartment rental

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £174 / night

£1213 - £1910 / week

Enquire View

from £174 / night

37

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

from £201 / night

£1406 - £2275 / week

Enquire View

from £201 / night

(1) Excellent 

24

Siesta Key holiday apartment rental

Florida / Siesta Key

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £119 / night

£749 - £1182 / week

Book View

Responds fast!
avg. 31 minutes

from £119 / night

10

Holiday condo in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £96 / night

£670 - £1178 / week

Book View

from £96 / night

(1) Very Good 

19

Holiday condo in Siesta Key

Florida / Siesta Key

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £46 / night

£320 / week

Book View

Responds fast!
avg. 2 hours 52 minutes

from £46 / night

(3) Excellent 

26

Siesta Key holiday condo rental

Florida / Siesta Key

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £87 / night

£552 - £985 / week

Book View

Responds fast!
avg. 2 hours 1 minutes

from £87 / night

(8) Excellent 

73

Holiday condo in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.01 km
  • Swimming pool
  • Child friendly

from £180 / night

£1260 - £1650 / week

Book View

Responds fast!
avg. 28 minutes

from £180 / night

(4) Excellent 

14

Holiday apartment in Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £166 / night

£1162 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £166 / night

(4) Average 

36

Siesta Key holiday apartment rental

Florida / Siesta Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £79 / night

£552 - £945 / week

Book View

from £79 / night

1