Vacation Rentals with Pool in Naples

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Filtering by: Swimming pool

1,951 vacation rentals

(4) Excellent 

15

Walk to Beach from Stunning Tropical Pool Home

Southwest Gulf Coast / Naples

Naples house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$205

Price per night from

$205

(11) Very Good 

35

Old Naples Luxury Cottage - Walk to 5th & Beach !

Southwest Gulf Coast / Naples

Naples house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Fab House, Fab Stay , Naples Great as ever.” We know Naples of old. What made our stay this time, was the fab Catterbox Cottage, great location, the right feel, the right decor and luxury level of comfort and facilities. Using a UK expression, the h
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Price per night from

$471

Responds fast!
avg. 25 minutes

Price per night from

$471

11

Beautiful 2 BR Condo in desirable Carlton Lakes, Naples

Southwest Gulf Coast / Naples

Naples condo

2 4 21 nights min

  • 2 bedrooms
  • sleeps 4
  • 21 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$71

Responds fast!
avg. 2 hours 12 minutes

Price per night from

$71

17

LUXURY RENTALS~ Sand Castle Beach House~Heart of Naples, close to beaches.

Southwest Gulf Coast / Naples

Naples house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,317

Price per night from

$1,317

(5) Very Good 

26

Naples - Vanderbilt Beach / Luxury Manager Villa

Southwest Gulf Coast / Naples

Naples house

4 11 min stay varies

  • 4 bedrooms
  • sleeps 11
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$527

Responds fast!
avg. 1 hour 51 minutes

Price per night from

$527

(17) Excellent 

15

Fresh and Bright, Ground Floor Condo, No Stairs.

Southwest Gulf Coast / Naples

Naples apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
“We felt like we were in Hawaii!!” Location was ideal. Closeness to pool was very important to us. Quietness from road traffic/noise was exceptional. Look forward to returning next winter.
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Price per night from

$102

Price per night from

$102

24

NEW! Premium 4BR Naples House w/Private Pool!

Southwest Gulf Coast / Naples

Naples house

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$258

Responds fast!
avg. 26 minutes

Price per night from

$258

(4) Excellent 

29

ALL NEW LUXURY CONDO IN FALLING WATERS RESORT. HUGE HEATED SALT WATER POOL.

Southwest Gulf Coast / Naples

Naples apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$109

Responds fast!
avg. 1 hour 3 minutes

Price per night from

$109

(2) Excellent 

36

Top Location, Best Views, Park Shore Resort 210

Southwest Gulf Coast / Naples

Naples condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$126

Responds fast!
avg. 30 minutes

Price per night from

$126

30

NEW! Expansive East Naples Home w/ Pool & Patio!

Southwest Gulf Coast / Naples

Naples house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$132

Responds fast!
avg. 22 minutes

Price per night from

$132

(7) Very Good 

25

Perfect Location Walk to Beach Heated Pool *Free Wifi* *Beach Supplies & Grill*

Southwest Gulf Coast / Naples

Naples house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Price per night from

$195

Responds fast!
avg. 28 minutes

Price per night from

$195

(1) Excellent 

17

Le Pelican Beach House ~ Private Beach ~

Southwest Gulf Coast / Naples

Naples house

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great Place!!!” Huge house! And GREAT location!! 5 Bedrooms and baths along w a HUGE room upstairs that has extra inflatable beds for kids. Pool is big and on the Naples bay, yet only about 5 blocks (1/2mile) from the beach. Also very close to both 3
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Price per night from

$916

Price per night from

$916

27

GOLFING, POOL, AND VACATION!

Southwest Gulf Coast / Naples

Naples house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$171

Price per night from

$171

5

Villa T's Naples

Southwest Gulf Coast / Naples

Naples house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child Friendly

Price per night from

$401

Price per night from

$401

(1) Excellent 

45

NEW AND CLEAN...WALK TO THE BEACH...ONE 25 LB PET ALLOWED...50% OFF MAY 9-NOV 30

Southwest Gulf Coast / Naples

Naples apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Price per night from

$114

Price per night from

$114

(16) Excellent 

12

Fountainview -3br/2ba Pool/spa home near the beach

Southwest Gulf Coast / Naples

Naples house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
“FOUNTAINVIEW TURNED INTO GARDENVIEW!!” so due to user error, gary moved us up a few streets to another rental!! let me tell you..... this house was perfect!! pool, hot tub, beach umbrellas, beach chairs, etc...if you needed it, this house had it waiti
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Price per night from

$201

Price per night from

$201

(3) Excellent 

19

New family friendly luxury home with private pool

Southwest Gulf Coast / Naples

Naples house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“A wondeful place to stay” We were two families with kids (12 years) who stayed for 2 weeks in April. The house is new, beautifully furnished and decorated and very clean, there is lots of space for 6 people. The kitchen is well equipped, there are pl
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Price per night from

$164

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$164

(1) Excellent 

28

Coral Falls condo w/incredible views of the pool/spa from private & well decorat

Southwest Gulf Coast / Naples

Naples apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
“Thanks for a wonderful week” I rented this condo for my parents and my aunt and uncle who were in Naples to celebrate their 50th wedding anniversary. They really loved everything about it. Clean, fresh, beautiful furnitured, everything you need in the
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Price per night from

$93

Responds fast!
avg. 12 minutes

Price per night from

$93

21

LUXURY RENTALS ~Royal Palm Beach House & Cottage

Southwest Gulf Coast / Naples

Naples house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$916

Price per night from

$916

(7) Excellent 

21

Next to Downtown and the Beach

Southwest Gulf Coast / Naples

Naples apartment

2 4 28 nights min

  • 2 bedrooms
  • sleeps 4
  • 28 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“Totally awesome, fun, great vacation!” Totally fell in love with this place. If you are looking for a 2 BR/2 bath condo in Naples, this is definitely the place to stay at. This is a corner unit, which is great, and recently updated and very very cle
…see more

Price per night from

$115

Price per night from

$115

10

GOLFING, POOL, AND VACATION!

Southwest Gulf Coast / Naples

Naples house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$143

Price per night from

$143

(15) Excellent 

24

Magnificent Pool Home Close to Beach and Downtown

Southwest Gulf Coast / Naples

Naples house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Will be back !” This was our second stay at this wonderful house - we loved it so much we are planning our vacation next year around it's availability ! Our thanks to all involved for making sure we had a terrific vacation. We travel a lot and I have
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Price per night from

$153

Price per night from

$153

(1) Excellent 

21

Beautiful condo

Southwest Gulf Coast / Naples

Naples house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Air conditioning
“Mrs.” Loved everything about this vacation rental. Awesome views, very bright and clean unit!!!! Easy access to beaches and shopping.
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Price per night from

$138

Responds fast!
avg. 1 hour 46 minutes

Price per night from

$138

37

Huge 3BR/2.5BA Southern Pool Home w/ Contemporary Design in beautiful Kings Lake

Southwest Gulf Coast / Naples

Naples house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$166

Responds fast!
avg. 1 hour 51 minutes

Price per night from

$166

13

LUXURY RENTALS~ Windstar Beach House~ Private beach!

Southwest Gulf Coast / Naples

Naples house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$966

Price per night from

$966

27

LUXURY RENTALS~The Bay House~Walk to beach & 3rd st shopping. Bring your boat!

Southwest Gulf Coast / Naples

Naples house

5 12 7 nights min

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

Price per night from

$1,489

Price per night from

$1,489

24

NEW! Prime 3BR Naples House Near Vanderbilt Beach

Southwest Gulf Coast / Naples

Naples house

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$212

Responds fast!
avg. 27 minutes

Price per night from

$212

(2) Excellent 

24

Enjoy a dream vacation in our vacation rental in Naples!

Southwest Gulf Coast / Naples

Naples house

4 10 7 nights min

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

Price per night from

$213

Responds fast!
avg. 1 hour 6 minutes

Price per night from

$213

(9) Excellent 

19

Charming Home on Southwestern Lake Close to Beach

Southwest Gulf Coast / Naples

Naples house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Naples House” This 4 bedroom was perfect for our family. The pool and lanai were beautiful- gorgeous sunsets. The house has a great layout and most everything you'll need. The beach is a little bit of a drive.
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Price per night from

$196

Price per night from

$196

19

LUXURY RENTALS~ Grand Floridian Beach House~ Beach views, Olde Naples

Southwest Gulf Coast / Naples

Naples house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,619

Price per night from

$1,619

(12) Excellent 

99

Falling Waters - ISLAND & WATER VIEWS Naples, FL

Southwest Gulf Coast / Naples

Naples apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
“A great vacation” This condo was everythng as promised! It was very clean when we arrived, the decor is very new and comfortable with a lot of natural light in the kitchen, living area and bedrooms. The vaulted ceilings created a feeling of spaciousne
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Price per night from

$77

Price per night from

$77

33

LUXURY POOL HOME

Southwest Gulf Coast / Naples

Naples house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$167

Price per night from

$167

21

LUXURY RENTALS~ Seaglass Plantation Beach House~Walk to beach and shopping!

Southwest Gulf Coast / Naples

Naples house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,626

Price per night from

$1,626

18

Carrington in Stonebridge

Southwest Gulf Coast / Naples

Naples house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children

Price per night from

$143

Price per night from

$143

36

Luxury Lake Home with Private Pool and Hot Tub and Great Amenities of The Quarry

Southwest Gulf Coast / Naples

Naples house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 16 mi
  • Swimming pool
  • Child Friendly

Price per night from

$161

Price per night from

$161

(20) Excellent 

15

Exquisite Naples Condo-Steps to the Beach

Southwest Gulf Coast / Naples

Naples apartment

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.32 mi
  • Swimming pool
  • Child Friendly
“our stay in unit 503 at The Regatta in Naples Florida .” We were completley satisfied with this condo . It had all the things were expected .we will be back next season.
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Price per night from

$295

Price per night from

$295

(3) Average 

23

5 bedroom pool home in Briarwood of Naples

Southwest Gulf Coast / Naples

Naples house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$171

Price per night from

$171

(1) Excellent 

39

Naples - Villa Noelia / Crown Pointe / Great Lake-view Pool Home

Southwest Gulf Coast / Naples

Naples house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“perfect house” the house was in a perfect condition , very nice furnished , clean , and everything was working perfect. The pool was very well maintained and a pleasure to swim in. We enjoyed the week of our stay and want to come back soon.
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Price per night from

$225

Responds fast!
avg. 1 hour 51 minutes

Price per night from

$225