50 Best Sanibel Island Vacation rentals on Holiday Lettings - Cottages

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2,030 Vacation rentals

9

Apartment accommodation in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This excellent Timeshare waterfront resort is set on a west coast island that is world-renowned for its shelling beaches. This ground floor condo is located in Lighthouse Resort and Club --a luxury waterfront resort on the world top rated Sanibel Island, Florida . The s …see more

from $210 / night

$1,050 / week

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from $210 / night

(3) Excellent 

26

Condo rental in Sanibel Island with golf nearby

Southwest Gulf Coast / Sanibel Island

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
This spacious (1500 sq ft) ground floor condo has been recently remodelled. It provides superb accommodation, sleeping up to 6 people in 3 bedrooms with 2 full bathrooms. Secure wi-fi is avalable in the condo. The condo is in an ideal island location - situated only a …see more

from $129 / night

$900 - $1,900 / week

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from $129 / night

(8) Excellent 

24

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Surfsound home is tucked away off Rabbit Road and is just a 5 minute walk to deeded beach access. This beautiful spacious home offers 3 bedrooms (1 US king, 1 queen and one twin), 3 ½ bathrooms, fully equipped kitchen private screened heated pool and beautiful décor. Su …see more

from $150 / night

$1,500 / week

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from $150 / night

24

Vacation condo with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
''DAYDREAMING'' BEACHFRONT condo is right on the Gulf of Mexico , you just can't get away from the beach . This beautiful one bedroom beach condo is tastefully furnished with a light , bright and sunny ambiance .The moment you walk through the door and see the beach you …see more

from $142 / night

$988 - $2,191 / week

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from $142 / night

(4) Excellent 

24

Vacation condo rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
'' SEAS THE DAY '' condo is right on the beach , on the Gulf of Mexico , you just can't get away from the beach , you can't get closer . This beautiful 1300 SQ.FT. 3rd floor CORNER UNIT condo with 2 verandas wrapping around it, giving it a great sense of space and ope …see more

from $213 / night

$1,488 - $3,338 / week

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from $213 / night

(1) Excellent 

24

Vacation condo with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
'' A STEP AWAY FROM THE BEACH '' is right on the beach , on the Gulf of Mexico , you step out the door and on to the beach , you can't get closer. This beautiful 1250 SQ.FT. ground floor , corner unit condo is well furnished with a light, bright and sunny ambiance. T …see more

from $213 / night

$1,488 - $3,338 / week

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from $213 / night

24

Vacation villa with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This recently redecorated south facing villa is situated in a quite but central part of Sanibel called Lake Murex . It is a spacious 4 bedroom, 3 full bath villa with a large open plan living area. The veranda overlooks the lake , the pool and the garden. There's a la …see more

from $200 / night

$1,398 / week

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from $200 / night

24

Home rental in Sanibel Island with golf nearby

Southwest Gulf Coast / Sanibel Island

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Lea by the Sea is a luxurious 5 BEDROOM beach house with its own private beach and large panoramic windows overlooking San Carlos Bay . The house was completely remodeled in 2010. It has flat screen televisions in all bedrooms and a 48 inch tv in the great room. It ha …see more

from $500 / night

$3,500 - $3,850 / week

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from $500 / night

28

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

4 10 30 nights min

  • 4 bedrooms
  • Sleeps 10
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A classic wooden Floridian house and guest house set on stilts in an acre of sub-tropical landscaped garden. Large outdoor, private, secluded raised pool with an expansive decking area consisting of a four-seater hot tub, recreation area and six sun beds. Five minutes w …see more

from $280 / night

$1,960 / week

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Responds fast!
avg. 1 hour 53 minutes

from $280 / night

15

Sanibel Island Vacation apartment accommodation

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
White Sands #12 - Stunning Gulf Front views This small condominium complex of 14 units in a very peaceful and relaxing location on West Gulf Drive is just east of Tarpon Bay Road. Make yourself at home in paradise in this nicely furnished 2nd floor 2 bedroom 2 bath wi …see more

from $215 / night

$1,505 - $3,187 / week

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from $215 / night

(4) Excellent 

21

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Enjoy the gorgeous views of San Carlos Bay in this 2 bedroom/2 bathroom condominium! You can watch the dolphins and manatees play, the fish jumping and the birds diving right from your private screened balcony! This condo is decorated in splashes of seafoam greens and f …see more

from $264 / night

$850 - $1,850 / week

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from $264 / night

(4) Very Good 

28

Vacation apartment with shared pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
GULF FRONT Cozy 1 bedroom ROMANTIC Condo - The best of old Sanibel with all NEW RENOVATIONS!! New carpeting, new bed and refrigerator!! Kimball Lodge at the Island Inn is the best of both worlds. This beautifully decorated 1 bedroom 1.5 bath GULF FRONT condo is in an ex …see more

from $200 / night

$917 - $2,121 / week

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Responds fast!
avg. 27 minutes

from $200 / night

(2) Excellent 

42

Vacation home with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
The Sand Castle, as we lovingly call our vacation house, is a beautiful single-family 3 bedroom / 2 bath luxury vacation house with magnificent views overlooking the greens and lakes of The Dunes, an 18-hole championship golf course and tennis club. The house has a la …see more

from $300 / night

$2,000 - $4,000 / week

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Responds fast!
avg. 3 hours 57 minutes

from $300 / night

(10) Very Good 

13

Home accommodation in Sanibel Island

Southwest Gulf Coast / Sanibel Island

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
There are only 7 cottages that make up this quiet Gulf access neighborhood. There is an on-site laundry facility and is conveniently located to bike paths, restaurants, shops and only a 3 minute walk across the street to the sugary white shell-filled beaches. This SMOKE …see more

from $242 / night

$750 - $1,700 / week

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from $242 / night

(2) Excellent 

21

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Condominium - 2 Bedrooms, 2 Baths, Sleeps 4 - 6, bay views from every room! Designer refurbished - May, 2014 This is our family's second home and our favorite place to be! It is a 1450-square-foot, two-bedroom, two-bath, luxurious, eighth-floor condominium at the newl …see more

from $422 / night

$2,959 / week

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from $422 / night

(6) Excellent 

23

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Come relax and enjoy paradise in this stylishly updated condominium in one of Sanibel's best locations. Professionally decorated in charming island style, this is the ideal tropical retreat to make your vacation getaway perfect. Open the doors on the lanai, and you will …see more

from $471 / night

$1,700 - $3,300 / week

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from $471 / night

25

Sanibel Island Vacation condo rental

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sanibel Arms West is a deluxe, beachfront condominium resort located right on the Gulf of Mexico with world famous white sand beaches. This spacious, two bedroom, vacation rental is perfect for families or groups offering all the amenities of home just yards from the be …see more

from $185 / night

$1,250 - $2,475 / week

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Responds fast!
avg. 53 minutes

from $185 / night

25

Vacation condo in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sanibel Arms West is a deluxe, beachfront condominium resort located right on the Gulf of Mexico with world famous white sand beaches. This spacious, two bedroom, vacation rental is perfect for families or groups offering all the amenities of home just yards from the be …see more

from $185 / night

$975 - $2,350 / week

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Responds fast!
avg. 54 minutes

from $185 / night

(2) Very Good 

30

Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Welcome to #1042 where it's "Just Another Day In Paradise" the theme of the decor for this fun, beachy, 2 bedroom/2 bathroom condo. There is a beautiful mural of palm trees as you walk in. To your right is the colorful kitchen which is fully equipped with all the essent …see more

from $264 / night

$850 - $1,850 / week

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from $264 / night

14

Sanibel Island Vacation cottage rental

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Suitable for children age 5+
Fully equipped beach cottage to make your vacation stay comfortable and effortless. Sanibel City ordinances permit a minimum stay of 28 days. Nerita Beach Cottage is just a short stroll to the beach. The home is just 10 houses to the beach. It features 2 bedrooms, one …see more

from $150 / night

$1,050 / week

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from $150 / night

(22) Excellent 

Certificate of Excellence

102

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Island Beach Club, 2265 WestGulf Drive, Sanibel. Beautiful ocean view penthouse level condominium located in the Island Beach Club next to exculsive Casa Ybel Resort on upscale West Gulf Drive. 2 bedrooms with ensuite baths. (great for couples or families) Beautifu …see more

Certificate of Excellence

from $200 / night

$2,400 - $2,800 / week

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Responds fast!
avg. 2 hours 27 minutes

from $200 / night

19

Home rental in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 21 nights min

  • 3 bedrooms
  • Sleeps 6
  • 21 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Beautiful Florida style home located on quiet and popular west-end of Sanibel Island. This is one of the most desirable neighborhoods on Sanibel. The home has vaulted ceilings, 3 bedrooms, 3 full baths, screened pool with waterfall hot-tub and is just a short walk to ac …see more

from $172 / night

$1,200 - $2,500 / week

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Responds fast!
avg. 2 hours 54 minutes

from $172 / night

18

Vacation home in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Home located in the Dunes, a golf course community, close to the bay and gulf beach. Bay beach is approx. 500 yards from the house and the gulf beach with private beach access is about 5 blocks. Home has 2 bedrooms + kids bunk room (1 king, 2 full/doubles, 2 twins) + …see more

from $83 / night

$625 - $1,550 / week

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from $83 / night

15

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This 2 bedroom 2 bath unit has panoramic views from lanai. Unit includes a den with room to relax. 2 flat screen TV's. Amenities include 2 tennis courts, a swimming pool, whirlpool and BBQ areas. A great family place that offers programs for children. Wireless int …see more

from $230 / night

$1,611 - $2,917 / week

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from $230 / night

24

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
This nice condo is located on the second floor with a view over the pool and courtyard out to the Gulf of Mexico. A very good value! The bedding is a king in the master, two twins in the guest and a sleeper sofa in the livingroom. 2 flat screen TV's. The condo sleep …see more

from $171 / night

$1,200 - $2,188 / week

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from $171 / night

19

Vacation home with swimming pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Location, location, location! A very, conveniently located 3 bedroom, 2 bathroom pool home just steps from West Gulf Drive's Beach Access #4! "Beach Time" is located in the most tranquil and desirable neighborhood on Sanibel directly off West Gulf Drive. The beach ac …see more

from $170 / night

$1,188 - $2,312 / week

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from $170 / night

27

Apartment rental in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
Looking for the best view the island has to offer? You found it! Enjoy the awesome 180-degree view of the Gulf of Mexico while you relax on the large wrap-around balcony. Start your day with a beautiful sunrise from the spacious master bedroom or while having coffee on …see more

from $300 / night

$2,100 - $4,000 / week

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from $300 / night

24

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Enjoy the best location in Sundial! This updated 3 bedroom, 2 bath corner unit, with wraparound lanai, offers stunning panoramic Gulf views from sunrise to sunset! Come and relax to the soothing sounds of the waves and bask in the refreshing Gulf breezes on the comforta …see more

from $286 / night

$2,000 - $3,950 / week

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from $286 / night

(1) Very Good 

21

Vacation apartment accommodation

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Sanibel Surfside is a 38 unit complex with pool, tennis courts and bbq grills and it is located off Donax and Middle Gulf Drive. This 2 bedroom 2 bath unit offers great views of the Gulf of Mexico. 3 flat screen TV's. Your home away from home! ********************* …see more

from $156 / night

$1,094 - $2,553 / week

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from $156 / night

21

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Pointe Santo is one of our most poplular properties. This very nice 3 bedroom 2 bath remodeled unit has beautiful views over the lake out to the Gulf of Mexico. 4 flat screen TV's 3 available with cable and 1 dvd only. 3 bedroom accommodations are hard to find - book …see more

from $214 / night

$1,498 - $3,525 / week

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from $214 / night

20

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Located on the 2nd floor with a Courtyard view from the lanai, this nicely updated condo has a living room, dining room and fully equipped kitchen. The bedding is a king in the master, 1 queen and 1 twin in the guest bedroom. 2 flat screens. One of our nicest! Log …see more

from $143 / night

$1,004 - $2,188 / week

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from $143 / night

19

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
This very nice 2 bedroom 2 bath with den (den closes off with sliding door) unit offers Gulf Views with easy access to the beach and pool. Perfect for those bikes, beach chairs and children's beach toys. Wireless internet connection is now available. As a guest of VIP …see more

from $208 / night

$1,458 - $3,161 / week

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from $208 / night

(7) Excellent 

23

Vacation home in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This beautiful 2 bedroom/2 bathroom condo sleeps up to six guests. It has a gorgeous well equipped modern kitchen with all new stainless steel appliances, granite counter tops, breakfast island, and tray ceiling lighting. The master bedroom has a king size bed, remote f …see more

from $371 / night

$1,300 - $2,600 / week

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from $371 / night

15

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
This is not your ordinary condo! This condo has been completely remodeled from the studs out, including new plumbing and electric, designed by award winning Joyce Owens Architect and Design. This spectacular 1 bedroom, 1 bath condo has wonderful views of the beach and t …see more

from $175 / night

$1,223 - $2,489 / week

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from $175 / night

(8) Excellent 

Certificate of Excellence

36

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
Enjoy your Sanibel vacation at the relaxing and quiet Breakers West complex in a unit that has seen many upgrades in the past year. This is a very spacious unit with 1,150 sq ft for you to relax in. The complex has a very private feel with only 18 units in the buildin …see more

Certificate of Excellence

from $205 / night

$1,230 - $2,580 / week

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Responds fast!
avg. 3 hours 11 minutes

from $205 / night

21

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Coquina Beach 5C is a very nice, updated unit with two bedrooms, two baths. 3 flat screen TV's. Located in one of Sanibel's most popular complexes Coquina Beach features a large pool and tennis. The unit is a very short distance to our world renowned shelling beaches …see more

from $141 / night

$985 - $1,969 / week

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from $141 / night

21

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This unit is located at the Sundial Beach Resort and is a spacious 3 bedroom, 2 bathroom condo that sits on the Gulf of Mexico with water views from the lanai. This condo offers over 1500 square feet of comfortable living space with a fully stocked kitchen and an open …see more

from $330 / night

$1,610 - $2,970 / week

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from $330 / night

18

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Steps from the beautiful sugar sand beach, this remodeled ground level 4 bedroom/3bath pool home offers the ultimate lifestyle for beach enthusiasts. Located within the seclusion of Sanibel's East end, this home features endless upgrades. PETS ALLOWED WITH OWNER APPRO …see more

from $166 / night

$1,162 / week

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from $166 / night

(8) Excellent 

21

Vacation home in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This island vacation property has 23 residences and is located on Middle Gulf Drive directly across the street from the Gulf of Mexico. Sandpepple sits on a canal where you may see many of the island tropical birds and other wildlife. You can enjoy watching them from th …see more

from $257 / night

$900 - $1,850 / week

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from $257 / night

27

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This nice unit has two bedrooms and two baths. 2 flat screen TV's. The unit offers views of the center courtyard area. Amenities include pool, tennis, BBQ, and shufflelboard. Loggerhead Cay is a 168 unit complex located directly on the beach near the entrance to Sa …see more

from $148 / night

$1,033 - $2,310 / week

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from $148 / night