50 Best Vacation Rentals in Southwest Gulf Coast - Holiday Lettings - Cabins

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Southwest Gulf Coast

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6,424 Vacation rentals

(2) Excellent 

22

Southwest Gulf Coast Vacation villa rental

Southwest Gulf Coast / Rotonda West

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
"Broad Key Villa" - Enjoy this luxurious, private villa located in a deed restricted community of Rotonda West on Florida's Gulf Coast, renowned for its numerous championship golf courses and beautiful soft, white, sandy beaches. Rotonda is the perfect location to sati …see more

from $253 / night

$1,767 / week

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from $253 / night

(30) Excellent 

24

Vacation villa in Fort Myers Beach

Southwest Gulf Coast / Fort Myers Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Island setting. 4 Bed, 2.5 Bath Villa, 8 minutes stroll from the lovely Fort Myers Beach. 33 Foot Infinity Pool with massage jets giving onto canal (dolphin+manatee visits). Extensive south facing Patio/Deck/Pool area with barbecue.Sleeps up to 8. Beach Equipment + Cadd …see more

from $228 / night

$1,595 - $2,445 / week

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from $228 / night

(3) Very Good 

16

Vacation home with swimming pool in Port Charlotte

Southwest Gulf Coast / Port Charlotte

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The cosy cottage is located in South West Florida more specifically in the beautiful port city of Port Charlotte. by 2015, the House was renovated and newly equipped with furniture, as well as a neugebautem pool area. The southern alignment makes it possible to relax yo …see more

from $78 / night

$535 - $670 / week

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avg. 1 hour 34 minutes

from $78 / night

(3) Excellent 

25

Vacation villa with golf nearby in Southwest Gulf Coast

Southwest Gulf Coast / Rotonda West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Situated in the quiet, residential area of Rotonda West, this prestine canal-side property is beautifully furnished and landscaped.LIVING AREASThe main living room includes comfortable sofas, 50-inch plasma TV featuring a comprehensive 180-channel Cable package and Bos …see more

from $120 / night

$835 - $882 / week

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Responds fast!
avg. 3 hours 34 minutes

from $120 / night

(14) Excellent 

Certificate of Excellence

26

Vacation home with golf nearby in Fort Myers

Fort Myers / South Fort Myers

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
Fort Myers is situated in the south west of Florida on the beautiful Gulf Coast, renowned for its long stretches of white sand and the warm waters of the Gulf Stream.Our modern two-storey house (2700 sq feet) is only 3 miles from Fort Myers Beach and 4 miles from the be …see more

Certificate of Excellence

from $126 / night

$921 - $993 / week

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from $126 / night

10

Home rental in Sarasota with indoor pool, golf nearby

Southwest Gulf Coast / Sarasota

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxury house with private pool situated on Tara golf and country club in Florida Bradenton. Our house is bright, spacious and fully air-conditioned. The house is furnished to a high standard throughout. There is a lounge with dining area. There is a large bright ful …see more

from $132 / night

$921 - $1,931 / week

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from $132 / night

(18) Excellent 

23

Vacation villa in Southwest Gulf Coast

Fort Myers / South Fort Myers

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
Our 3 bed/2 bath house in South Fort Myers is within easy reach of the stunning beaches of Fort Myers Beach, Sanibel and Captiva. Situated in the quiet and sought-after residential area of Wellington it is tastefully furnished and provides a comfortable home from home …see more

from $125 / night

$875 - $915 / week

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Responds fast!
avg. 3 hours 40 minutes

from $125 / night

(15) Excellent 

25

Vacation home accommodation

Fort Myers Beach / Estero Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Bay Front Dream Home. If the water is your passion, come stay in this beautiful bayfront home. Bring your morning cup of coffee to the screen-enclosed pool and lanai to watch the sunrise over Estero Bay. Enjoy fishing from the boat dock, watch the dolphins or its just …see more

from $291 / night

$2,033 - $3,409 / week

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from $291 / night

(10) Excellent 

40

Southwest Gulf Coast Vacation guest house rental

Southwest Gulf Coast / Cape Coral

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
This ad is for a room. Our guesthouse is newly renovated, completely covered with glossy tiles, lies close to the island of Pine Iceland and the Kuenstlerviertel in Key West style on Matlacha. Our rooms are bright and friendly. The sandy beach on the marina is roughly a …see more

from $39 / night

$259 / week

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Responds fast!
avg. 3 hours 43 minutes

from $39 / night

(15) Very Good 

30

Vacation villa in Southwest Gulf Coast

Southwest Gulf Coast / Cape Coral

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
Our newly remodeled Villa has about 2,000 sq.ft. Living area with 1,100 sq.ft. Generous pool area. You will be love the heated pool with the separate Scandinavian style SPA (Jacuzzi). Within only 3 minutes by boat you’ll reach the high-speed areas on Caloosahatchee Rive …see more

from $140 / night

$980 / week

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from $140 / night

(1) Excellent 

35

Southwest Gulf Coast Vacation home rental

Fort Myers Beach / Estero Island

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
One of two identical homes with shared patio and pool. White, sandy beach in a short, walking distance (3 minutes). The private island on the nature lake perfectly suits for fishing. Me and my wife love traveling, and one of the places that we love to return every y …see more

from $299 / night

$2,093 / week

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Responds fast!
avg. 3 hours 40 minutes

from $299 / night

43

Vacation apartment in Southwest Gulf Coast

Southwest Gulf Coast / Naples

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Our condo at the World Tennis Club in Naples, Florida, is spacious and luxurious with a large lounge/diner with comfortable sofas and dining for 6. Patio doors give access to a screened balcony/lanai with views over a lake. Herons, egrets, Ibis, ducks and otters inhabit …see more

from $86 / night

$597 - $835 / week

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Responds fast!
avg. 2 hours 48 minutes

from $86 / night

49

Villa rental in Southwest Gulf Coast

Southwest Gulf Coast / Cape Coral

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The newly built dream mansion that stands in November 2017 your vacations, is located in a beautiful location right on the Caloosahatchee River, which empties into the Gulf of Mexico. Close by, about 5 minutes. on foot, the only sandy beach invites directly into Cape Co …see more

from $404 / night

$2,826 - $3,911 / week

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from $404 / night

(20) Excellent 

Certificate of Excellence

16

Vacation apartment in Southwest Gulf Coast

Southwest Gulf Coast / Bradenton

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
Our light, spacious, open-plan apartment is in the Shorewalk complex, situated on the beautiful central Gulf Coast of Florida.  Shorewalk comprises 2-story buildings on 30 acre grounds with mature trees.  Paths, well-lit at night, meander around 6 stocked lakes to lead …see more

Certificate of Excellence

from $88 / night

$596 - $881 / week

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from $88 / night

29

Southwest Gulf Coast Vacation home rental

Southwest Gulf Coast / Bonita Springs

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 7 mi
  • Swimming pool
  • Child friendly
Gorgeous new home with awesome amenities.12 foot coffered ceilings Large shower and bidet in Master bathroom High speed internet with WiFi (WLAN) extender so that you maintain a strong signal even in the lanai/pool area. 65" 4K TV's in Master Bedroom and Great Room Cage …see more

from $130 / night

$910 / week

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from $130 / night

(7) Excellent 

17

Cape Coral Vacation home rental

Southwest Gulf Coast / Cape Coral

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
Luxury Villa with waterfall pool! Our villa offers a stylish ambiance and exclusive equipment for demanding people. The villa is on a 1000 m² tropical garden plot in the heart of Cape Coral, very quiet. On 190 sqm air-conditioned living space offers 3 cozy luxury bedroo …see more

from $116 / night

$813 / week

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from $116 / night

(2) Excellent 

29

Vacation villa in Cape Coral

Southwest Gulf Coast / Cape Coral

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The elegant villa is located in the southernmost and therefore interesting part of Cape Coral. Dream view of the water: It is one of the few head land on Nimrod channel. From the dock, and the 25-meter Captain Walk you can watch dolphins and Manetees, fishing and enjoyi …see more

from $244 / night

$1,866 - $2,677 / week

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Responds fast!
avg. 2 hours 17 minutes

from $244 / night

(31) Excellent 

24

Vacation villa in Southwest Gulf Coast

Southwest Gulf Coast / Rotonda West

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
The Villa is beautifully furnished and equipped to a very high standard as our second home, it is fully air conditioned throughout and has ceiling fans in each room for added comfort. We have also taken the extra step of having a Titanium coating on the villa windows to …see more

from $106 / night

$729 - $921 / week

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from $106 / night

(20) Excellent 

22

Vacation villa with golf nearby in Southwest Gulf Coast

Rotonda West / Broadmoor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
This privately own Villa is rented directly from its U.K. owners with no agents or commissions. It is maintained in lovely condition by the owners and their local professional management company who are always available should you need help or advice. This …see more

from $95 / night

$663 - $1,067 / week

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Responds fast!
avg. 2 hours 7 minutes

from $95 / night

(6) Excellent 

24

Vacation apartment in Bradenton

Southwest Gulf Coast / Bradenton

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a brand new coach home (built 2013) 2,515 Sq. Ft. Including a two car garage of 376 Sq. Ft. It has a private entrance and is located on the ground floor. Once you enter the Foyer you overlook a beautiful Living Room mostly furnished with dark brown le …see more

from $122 / night

$850 / week

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from $122 / night

(1) Excellent 

15

Vacation home in Port Charlotte

Southwest Gulf Coast / Port Charlotte

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
This small house is in a beautiful neighborhood in the beautiful Port Charlotte. In September 2016, was completely refurbished. Info House: 95 sqm living area about 900 square meters of land climate control, ceiling fans and smoke detectors occupancy max. 4 adults cover …see more

from $98 / night

$683 / week

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from $98 / night

(2) Excellent 

10

Vacation villa with golf nearby in Southwest Gulf Coast

Southwest Gulf Coast / Rotonda West

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Sunset Pines - Located just a short driving distance away from the beach, this beautiful vacation villa in Rotonda is an excellent get away for you. This three bedroom home is perfect to sleep up to six guests. The master bedroom includes a king size bed, and the othe …see more

from $199 / night

$1,390 / week

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from $199 / night

34

Villa rental in Englewood

Southwest Gulf Coast / Englewood

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Total Retreat - Beautiful Lake Marlin Waterfront Home, close Beaches & Shopping Beautiful Lake Front Estate Home on Lake Marlin 3-D Walkthrough Available... 3-D Walkthrough - Click on the video link on the Photo labelled "Fun Rental" to see a beautiful 3-D video wa …see more

from $166 / night

$1,127 / week

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from $166 / night

(5) Very Good 

34

Villa rental in Rotonda West with golf nearby

Southwest Gulf Coast / Rotonda West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool
The newly furnished home located on a freshwater canal in Rotonda West, a wonderful golfer friendly community with 5 golf courses in the immediate vicinity of the house and 15 other reach within 25 minutes. New electric pool heater from 20. 12. 2013 additionally added t …see more

from $125 / night

$871 - $1,300 / week

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from $125 / night

26

Villa rental in Cape Coral

Southwest Gulf Coast / Cape Coral

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
Our in 2002 built dream home with 3 bedrooms, 2 bathrooms and 3 garages was currently completely refurbished and offers on 1500 sqm plot and 180 sqm living space everything your heart desires. In addition, the large terrace with large swimming pool, garden furniture, ch …see more

from $149 / night

$1,044 - $1,670 / week

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from $149 / night

26

Condo rental in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
AKA the "Green Roof Condos", we are a 1000 sq ft end unit with no one above or below. South facing and perched 20 feet above the ground with palm trees in all views. There is a second floor loft (fixed ladder) that sleeps 2. We have a freshwater pool right on the island …see more

from $129 / night

$1,000 - $1,750 / week

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avg. 2 hours 47 minutes

from $129 / night

(4) Excellent 

24

Vacation villa with indoor pool in Southwest Gulf Coast

Southwest Gulf Coast / Bradenton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Spacious Villa 4 bed, 2 bath, front lake view, BBQ Grill, Lanai, up to 8 people Relax at your pool and admire at the same time the lake view with herons !!! Great location just a short drive to amazing beaches, great restaurants and shopping, 15 minutes from downtown …see more

from $117 / night

$819 / week

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from $117 / night

23

Vacation villa rental

Southwest Gulf Coast / Rotonda West

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Halcyon Days - An executive built and spacious home with high cathedral ceilings, which sleeps 8-10, has a screened in front porch and large 50' caged lanai and pool deck. The split floorplan of master suite to one side of the great room and the other bedrooms and bathr …see more

from $237 / night

$1,658 / week

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from $237 / night

(4) Excellent 

16

Vacation villa rental

Southwest Gulf Coast / Naples

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
SEASON 2019 - CASA NAPOLETANA Lovely detached villa 4/3 with pool, hot tub & lake view in a secure community of Artesia, Naples. The house with its 4 bedrooms and 3 bathrooms easily accommodates 8 people New furniture in the lounge: sofa, love seat, fautauill , coffe …see more

from $175 / night

$1,350 - $2,050 / week

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from $175 / night

(31) Excellent 

24

Englewood holiday villa rental with swimming pool

Southwest Gulf Coast / Rotonda West

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
Built and furnished to the highest standards our luxury 3 bedroom villa with private solar heated pool is the ideal place to relax and unwind. Our exclusive custom built villa overlooks a secluded lake and Golf Course to the rear. Our home has spacious fully air condi …see more

from $92 / night

$663 - $729 / week

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Responds fast!
avg. 2 hours 59 minutes

from $92 / night

(1) Excellent 

22

Vacation home rental

Southwest Gulf Coast / Port Charlotte

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Chaves - Vacation home near beach und golf course Approx. 1205 sqft under air, 1 living room, 2 bed rooms with built-in closets, 1 study, 2 bath rooms (thereof one with shower, one with shower & tub combination), 1 kitchen, 1 garage (approx. 215 sqft)., lanai (roofed) …see more

from $110 / night

$660 - $900 / week

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from $110 / night

(6) Very Good 

Certificate of Excellence

12

Vacation villa in Southwest Gulf Coast

Port Charlotte / South Gulf Cove

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
A stunning 4-5 bed home with 2 amazing master en suites. South facing pool & spa overlooking woodland. A perfect, quiet, restful setting to enjoy the delights of the South West cost of Florida in what really is a perfect home. Everything you could wish for is here read …see more

Certificate of Excellence

from $109 / night

$1,160 / week

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Responds fast!
avg. 2 hours 35 minutes

from $109 / night

(8) Excellent 

9

Vacation villa rental

Rotonda West / Rotonda Lakes

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
Situated lakeside this home has everything to ensure your vacation is as relaxing and comfortable as you would want it to be. A true home from home! Have fun in, or simply relax by the heated pool. The pool and lanai areas are completely screened. You can …see more

from $93 / night

$597 / week

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Responds fast!
avg. 2 hours 42 minutes

from $93 / night

(11) Excellent 

24

Vacation villa with golf nearby in Southwest Gulf Coast

Rotonda West / Broadmoor

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
The stylish Villa Merindah is situated in Rotonda West, a delightful community located on the Cape Haze Peninsula, South Gulf Coast of Florida, close to Tampa and Fort Myers international airport We called our villa "Merindah" which means beautiful / happy because, a …see more

from $120 / night

$835 / week

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Responds fast!
avg. 3 hours 0 minutes

from $120 / night

(1) Excellent 

16

Home rental in Southwest Gulf Coast

Southwest Gulf Coast / Cape Coral

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
Very nice Off Water Non smoking holiday house about 200 m² with heated pool in quiet location. The house has 3 bedrooms and 2 bathrooms. The interior of the house is decorated in a tasteful brown and beige. In the extension of the kitchen invites cozy dining room overlo …see more

from $116 / night

$730 - $893 / week

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from $116 / night

(2) Excellent 

34

Vacation villa in Southwest Gulf Coast

Fort Myers / South Fort Myers

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in the ever popular South Fort Myers area of Florida, the home is ideally situated close to all local amenities, outlet malls, restaurants shops and recreational activities are a short jog away. The Islands of Sanibel and Captiva, and the beautiful beaches of Fo …see more

from $133 / night

$928 / week

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from $133 / night

12

Vacation apartment in Southwest Gulf Coast

Southwest Gulf Coast / Englewood

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The apartment is in a very nice community with a predominantly elderly residents, but children are welcome. It is fully equipped, also with beach towels, beach chairs and a cool box. From the balcony (with fly screen) You have a great view of the canal, also from the ma …see more

from $71 / night

$496 - $918 / week

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from $71 / night

12

Home rental in Englewood

Southwest Gulf Coast / Englewood

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Our house is right on the boat slip, has an inflatable canoe and two bicycles. The residential area is quiet, the beach is about 2 miles. It is fully equipped to local stations can be received, WiFi via a router with prepaid access. We offer the possibility to clean the …see more

from $61 / night

$423 - $918 / week

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from $61 / night

14

Vacation home rental

Southwest Gulf Coast / Cape Coral

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The house is located on a canal. from which one can reach the Gulf of Mexico by boat. It is in a very quiet residential area. Shops are nearby. The house has a double garage, fully furnished and has washer and dryer and kitchen with microwave, oven, refrigerator and eve …see more

from $232 / night

$871 - $1,729 / week

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from $232 / night

(19) Excellent 

22

Southwest Gulf Coast Vacation apartment rental

Southwest Gulf Coast / Sarasota

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Family friendly beautiful & charming paradise The Coastal Manor of Sarasota is situated on a small waterway that leads to the Bay of Sarasota. Sports and shopping are also within walking distance. At our pool you can relax after your day. Children are welcome. For our y …see more

from $175 / night

$1,225 - $2,450 / week

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from $175 / night