50 Best Naples Vacation rentals on Holiday Lettings - Apartments

Close

View larger map

Also consider

Naples Beach
18 properties
Vanderbilt Beach Area
5 properties

Naples

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

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

514 Vacation rentals

Travelers going to Naples are booking March dates now. Secure your vacation rental today and have the perfect trip.

(12) Very Good 

28

Villa rental in Naples with golf nearby

Naples / Lely Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
This beautiful, three bedroom home is both spacious and well-designed. Built in 2003, it provides all the modern amenities you would expect in a family home. It also has a large heated private pool and spa with screened lanai overlooking a tranquil lake. Both pool and l  …see more

from $165 / night

$1150 - $1850 / week

Book View

from $165 / night

22

Villa rental in Lely Resort with golf nearby

Naples / Lely Resort

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
DEAL ALERT!! This property very rarely has peak season availability...however I have a last minute cancellation for the first two and a half weeks of December 2015. As an incentive I am offering a 20% discount for booking these dates (1 - 19 December 2015).******  …see more

from $215 / night

$1500 - $2301 / week

Book View

from $215 / night

14

Vacation villa with golf nearby in Naples

Naples / Naples Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Westlake Villa offers guests a lovely comfortable vacation home full of old Naples charm. It has 3 bedrooms, the master suite with king sized bed is en-suite and has a flat screen TV. The queen has a flat screen tv and twin room has a dvd flat screen tv, there is a 2nd  …see more

from $124 / night

$986 - $1364 / week

Inquire View

from $124 / night

(4) Excellent 

27

Vacation villa rental

Naples / Briarwood

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
BACK ON THE MARKET FROM JUNE 2016!!!! Lovely detached villa vith large pool in a secure community in Naples, Briarwood. There are 3 bedrooms and 2 bathrooms. Living room: 2 sofas, coffee table, TV, tv-stand. Working space with desck, PC and printer. Kitchen with all ap  …see more

from $98 / night

$698 - $1701 / week

Book View

from $98 / night

(1) Excellent 

11

Home rental in Naples with golf nearby

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool
We overlook the beautiful Hibiscus Golf Course in the famous Lely Area. Our single family pool home has three bedrooms and open plan living space of 2000 square feet. A magnificent chefs kitchen area should you want to wine and dine. It boasts 1800 of outdoor living sp  …see more

from $186 / night

$1240 - $1488 / week

Book View

from $186 / night

21

Vacation condo in Naples

Southwest Gulf Coast / Naples

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a 1st floor 3 bedroom 2 bathroom condo situated in the Lely Landing community, there are only 24 condos which are built around the clubhouse. The communal pool is only a few minutes walk away, fabulous location the pool captures the sun all day, sun loungers are  …see more

from $89 / night

$620 / week

Book View

from $89 / night

4

Vacation apartment in Naples

Southwest Gulf Coast / Naples

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
On the bay in Olde Naples within easy walking distance of the excellent shops and restaurants of Fifth Avenue and Third Street, as well as the beach and pier, famous for viewing the sunset. Adjacent small park with larger park close by with bandshell for regular concert  …see more

from $251 / night

$1750 / week

Book View

from $251 / night

21

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Beautiful lake view, safe gated community, comfortable for seniors, ground floor with walkout from lanai, kind neighbours, walking distance from groceries / drug store, 10 minutes from beautiful Gulf beaches. Tons of fabulous restaurants and fun things to do. (1.5 Hou  …see more

from $54 / night

$374 / week

Book View

from $54 / night

(8) Excellent 

29

Naples / Vanderbilt Beach Area

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $165 / night

$1150 - $1373 / week

Book View

from $165 / night

20

Naples Vacation villa accommodation

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Westlake Villa offers guests a lovely comfortable vacation home full of old Naples charm. It has 3 bedrooms, the master suite with king sized bed is en-suite and has a flat screen TV. The queen has a flat screen tv and twin room has a dvd flat screen tv, there is a 2nd  …see more

from $133 / night

$930 - $1178 / week

Book View

from $133 / night

24

Naples / Naples Beach

3 6 Min stay varies

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

 …see more

from $170 / night

$1188 / week

Book View

from $170 / night

12

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
Abaco Bay is a Key West inspired community in an ideal central Naples location. Less than 5 minutes from the Gulf of Mexico and its pristine beaches and shopping and fine dining nearby off 5th Avenue (the heart of Historic Downtown Naples) and 3rd Street South. Abaco B  …see more

from $51 / night

$351 / week

Book View

from $51 / night

(1) Excellent 

21

Apartment rental in Lely Resort with golf nearby

Naples / Lely Resort

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxury apartment in Treviso Bay world class TPC golf and country club community with beautiful resort pool and state of the art fitness facilities. Overlooking the Rookery Bay preserve and close to downtown Naples and beaches it offers the best of all worlds for your Fl  …see more

from $84 / night

$584 / week

Book View

from $84 / night

14

Vacation home with golf nearby in Naples

Southwest Gulf Coast / Naples

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Our Villa is a luxury home, with full air conditioning set in the small-gated community situated within Lely Resort Golf and Country Club, Just minutes from beautiful beaches, Fifth Avenue shops, Naples Pier, Marco Island, World Class Golf Courses, and numerous fine din  …see more

from $169 / night

$1178 - $1364 / week

Book View

from $169 / night

(14) Excellent 

26

Vacation villa in Naples

Southwest Gulf Coast / Naples

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Conway House is a fantastic family holiday home situated in a private location in old Naples. Whilst the house is central (only 5 mins drive to the beach and to the Coastland shopping centre) it is in a very quiet residential area and backs onto a lagoon. The villa is  …see more

from $143 / night

$1001 - $1880 / week

Inquire View

from $143 / night

18

Villa rental in Naples with golf nearby

Southwest Gulf Coast / Naples

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Augusta Falls could not be better located in Naples as it is short walk of a large shopping centre, less than a mile from an interstate junction, very much in the centre of Naples, yet on one of Naples most well known sought after secure gated golf communities. Thus pea  …see more

from $155 / night

$1085 - $1234 / week

Book View

from $155 / night

14

Vacation home in Naples

Southwest Gulf Coast / Naples

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Home is located in a residential neighborhood 0.5 miles from private park (for owners and their guests ) adjacent to the beautiful Naples beach. We are also 0.5 miles from shopping, grocery store and restaurants. This home has been recently renovated with all new air-co  …see more

from $315 / night

$2201 / week

Book View

from $315 / night

44

Vacation apartment with golf nearby in Naples

Naples / Naples Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
SPECIAL RATES starting MAY!!! This property is only for non-smokers. Pets are not allowed. Holiday period normally requires a minimum of 30 days, however a 14 day may apply according to booking. Please ask! The apartment is located in a residence that is part of one of  …see more

from $200 / night

$1400 - $1601 / week

Book View

from $200 / night

(7) Very Good 

10

Vacation home in Naples

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
This is a 2 bedroom, 2 bath, private pool home in Southwest Florida, located in a quiet residential neighborhood called Bonita Shores, West of Hwy. 41. Within walking distance to the beach. Just a few miles north of Naples in Collier county, this home (house) is within  …see more

from $122 / night

$851 - $1150 / week

Inquire View

from $122 / night

12

Naples Vacation apartment rental

Southwest Gulf Coast / Naples

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Amazing 2 bedroom, 2 bath super LUXURIOUS corner apartment with soaring double height (18 feet) ceilings with an unbelievable Miami skyline view from all rooms. Sophisticated, fully high-end designer furniture from TUI and appointed on the 40th floor. - Fabulous Tui Li  …see more

from $401 / night

$2751 - $3450 / week

Book View

from $401 / night

(2) Excellent 

19

Vacation home in Naples

Southwest Gulf Coast / Naples

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Be one of the first people to live in this beautiful, brand new luxury home in the community of Hawthorne. The home was finished in December 2013 and comes fully furnished and designed by Pottery Barn. The master bedroom features a king size bed and two walk-in clos  …see more

from $280 / night

$1960 / week

Book View

from $280 / night

24

Apartment rental in Naples with golf nearby

Southwest Gulf Coast / Naples

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Air conditioning
Unique chance to stay at a gorgeous luxury apartment with a touch of elegance and impressive water & city views of Miami's upscale Brickell and the Atlantic Ocean. Enjoy the quality of a 5 star hotel in a luxurious, impeccable and comfortable condo, with Itali  …see more

from $172 / night

$1201 / week

Book View

from $172 / night

(4) Excellent 

36

Naples Vacation home rental

Southwest Gulf Coast / Naples

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This gorgeous high spec 2000 sq ft 2 bedroom, 2 bathroom house in East Naples has been completely remodeled in 2015. Situated in the exclusive Woodlands development in Kings Lake, Naples, this bright, beautiful Florida home is available for rental from October 2015. The  …see more

from $179 / night

$1251 / week

Book View

from $179 / night

17

Vacation villa rental

Southwest Gulf Coast / Naples

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
The Briarwood villa, yet another beautiful, well kept home in the heart of Naples offers both superb accommodation, great south facing views, privacy, security and close proximity to heart of Old Naples. This spacious 4 bed 3 bath home is within the community of Briar  …see more

from $159 / night

$1110 - $1922 / week

Book View

from $159 / night

(1) Excellent 

10

Southwest Gulf Coast / Naples

2 6 5 nights min

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

 …see more

from $133 / night

$928 / week

Book View

from $133 / night

17

Naples / Vanderbilt Beach Area

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $84 / night

$584 / week

Book View

from $84 / night

20

Naples Vacation villa rental

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Our Villa is a lovely luxury villa set in the small gated community of Masters Reserve situated within Lely Resort Golf and Country Club. The villa has 3 good-sized bedrooms and 2 bathrooms. Apart from the high specifications of the property it benefits from being in a  …see more

from $178 / night

$1240 / week

Book View

from $178 / night

19

Vacation apartment with indoor pool in Naples

Southwest Gulf Coast / Naples

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
LAST MINUTE AVAILABILITY XMAS & NY!!! ALSO LONG TERM RENTAL POSSIBLE. PLEASE INQUIRE ABOUT DISCOUNTED RATES FOR LONGER STAYS AND SPECIAL PRICES FOR OFF-PEAK DATES If you want LUXURY pure this is the one for you! Many people rent this one for special occasions as i  …see more

from $434 / night

$3100 / week

Book View

from $434 / night

22

Vacation apartment with golf nearby in Naples

Southwest Gulf Coast / Naples

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
A beautiful 2 bedroom plus den 2 bathroom condominium on Falling Waters, Amelia Lake ,Davis Boulevard, Naples - a stunning, world class gated resort complex themed around tropical gardens and waterfalls with one of the largest and most photogenic swimming pools in SW Fl  …see more

from $88 / night

$614 - $1054 / week

Book View

from $88 / night

17

Villa rental in Naples with golf nearby

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
This is a stunning 3 bedroom/2 bathroom villa in Masters Reserve, Lely, Naples. The master bedroom has a king sized bed, patio doors, TV, Telephone and full ensuite bathroom with walk in shower. Bedroom 2 has a queen bed with bay window; bedroom 3 has two single beds.  …see more

from $151 / night

$1054 - $1426 / week

Book View

from $151 / night

28

Vacation home with golf nearby in Naples

Southwest Gulf Coast / Naples

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
If you love the beach, fine dining and shopping, but like the privacy and comfort of a single home, then our luxury 3 bedroom, 2 bathroom villa with a private screened, heated pool is a perfect choice. The house is located 3/4 miles from Vanderbilt Beach in Naples near  …see more

from $215 / night

$1500 - $2401 / week

Book View

from $215 / night

5

Home rental in Naples

Southwest Gulf Coast / Naples

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Child friendly
Please note this home was rented in Jan 2016 for for the January 2017season and has just come back on the market. It is available from Jan 2 2017 for the season. The perfect winter getaway in Fiddler’s Creek awaits you in this outstanding single family, former sh  …see more

from $200 / night

$1400 / week

Book View

from $200 / night

27

Home rental in Naples

Southwest Gulf Coast / Naples

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
If you love the beach, fine dining and shopping, but like the privacy and comfort of a single home, then our luxury 3 bedroom, 2 bathroom villa with a private screened, heated pool is a perfect choice. The house is located 3/4 miles from Vanderbilt Beach in Naples near  …see more

from $215 / night

$1500 - $2201 / week

Book View

from $215 / night

(3) Excellent 

20

Southwest Gulf Coast / Naples

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool

 …see more

from $51 / night

$401 - $745 / week

Book View

from $51 / night

(3) Excellent 

87

Southwest Gulf Coast / Naples

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 7 mi
  • Swimming pool
  • Air conditioning

 …see more

from $140 / night

$875 - $1504 / week

Book View

from $140 / night

14

Southwest Gulf Coast / Naples

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly

 …see more

from $251 / night

$1001 - $1500 / week

Book View

from $251 / night

27

Southwest Gulf Coast / Naples

3 6 7 nights min

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

 …see more

from $171 / night

$1201 - $3200 / week

Book View

from $171 / night

(3) Very Good 

18

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $251 / night

$1500 - $2500 / week

Book View

from $251 / night

(4) Very Good 

19

Southwest Gulf Coast / Naples

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $100 / night

$700 - $1156 / week

Book View

from $100 / night

28

Southwest Gulf Coast / Naples

Studio 3 5 nights min

  • Studio
  • Sleeps 3
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $120 / night

$840 / week

Book View

from $120 / night