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iTrip Fort Myers + SWF Vacation Rentals

iTrip Fort Myers + SWF Vacation Rentals

Member since 2023
95 rentals
35 reviews
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Bonita Springs Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Start your morning with coffee on the lanai overlooking the pool. Spend the day on the beach just across the street. End the evening with a cocktail and a Gulf sunset at Doc's Beach House — literally across the road. This 5th floor studio at Bonita Beach & Tennis Club makes that kind of...

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Featured review

"Beach Get Away"

We wanted a few days on the beach and this rental fulfilled this requirement. It is just across the road from Barefoot Beach.

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$130
avg per night
Bokeelia House
Sleeps 5, 2 bedrooms, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Tarpon Camp in beautiful Bokeelia, FL - your own private retreat in the heart of the Tarpon Capital of the World!Nestled in the small fishing village of Bokeelia, on the north end of Pine Island, this cottage has quick access to Shell Pass, Pine Island Sound, Charlotte Harbor, Cayo Costa...

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Featured review

"Tarpon house"

House was clean and supplies were plentiful. Directions and lock on front door were great. Boat dock awesome quiet good parking. Nothing wasn’t thought of when this home was done over. Thanks guys...

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$165
avg per night
Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

From the 7th floor of this Lovers Key Resort condo, the view takes in two of Southwest Florida's most beautiful destinations at once — Estero Bay spreading out below and the southern end of Fort Myers Beach stretching to the north. Watch for dolphins moving through the Bay in the morning light....

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$142
avg per night
Fort Myers Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

STR # R250077The higher the floor, the wider the Gulf spreads out before you — and from the 6th floor of Estero Island Beach Villas, the view from the screened lanai is genuinely breathtaking. The entire western horizon is yours, the beach stretches below in both directions, and every evening...

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Featured review

"Great location and view"

We enjoyed our stay in this Beach Villas condo. Beautiful view of rhe gulf and so fun to he next door to pink shell resort where we could hear the music and waterfalls over their pool. This condo complex...

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$294
avg per night
Bonita Springs Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This beautiful condo has been remodeled since the recent hurricane's and is available for rental occupancy - the pool, fitness center, game room, BBQ grill and beach are open!Bonita Beach Club continues to rebuild while re-opening since recent hurricanes. Bonita Beach Club is still considered...

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Featured review

"Great place to stay!"

Our stay was short but sweet. We enjoyed the pool and the lanai was our go-to hang out spot. Plenty of towels and wash cloths were provided which we really appreciated. The one little hiccup in our delightful...

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$136
avg per night
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

STR # R260360The Bay Village Condominium is still doing some minor post hurricane repair work on the common areas to include the Sauna. As a result, the condo HOA is requiring all owners, guests & renters to sign a construction disclaimer/waiver prior to occupancy. Management will send a copy...

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$129
avg per night
Fort Myers Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

You’ve just found your perfect Southwest Florida getaway! Located in the desirable South Fort Myers area, this vacation condo is set within the private, gated community of Tortuga. An enclave of attached villas and condominiums, Tortuga offers the welcoming feel of a close-knit neighborhood along...

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$90
avg per night
Bonita Springs Condo
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The Bonita Bay private beach club has just re-opened! Be among the first to experience the stunning, private Bonita Beach Club and shoreline access reserved exclusively for owners and guests at Bonita Bay. A luxurious experience many can only dream of can be yours during your stay!The Condo -Welcome...

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$268
avg per night
Bonita Springs Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The Gulf is sparkling just across the street, the sunsets are unforgettable, and this beautifully remodeled studio at Bonita Beach & Tennis Club is ready to deliver one of the most comfortable, well-appointed beach getaways on the property. Whether you're here for a long weekend or an extended...

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$135
avg per night
Bonita Springs Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Start your morning with a Keurig or a full drip pot — this thoughtfully updated 7th floor studio in Building 3 at Bonita Beach & Tennis Club has both covered. With a king bed, a bathtub for long soaks after beach days, a Smart TV, a desk alcove for remote workers, and the white sands of Bonita...

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$119
avg per night
Cape Coral House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Slow down, soak up the sunshine, and settle into the laid-back Southwest Florida lifestyle at this welcoming Cape Coral pool home. Tucked into a desirable Southwest Cape neighborhood lined with tropical palms and canals, this comfortable retreat offers the perfect home base for beach days, boating adventures,...

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$165
avg per night
Cape Coral House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to sunny Southwest Florida and settle into this beautifully remodeled pool home in desirable SW Cape Coral — a spacious, stylish retreat designed for easy vacation living, poolside relaxation, and memorable time together with family and friends. With over 2,100 square feet of bright open...

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$174
avg per night
New
Fort Myers Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

*The condo building exterior is being pressure washed and painted between April 8-24, 2026. However, the condo may be occupied and the beach is accessible during this time.Enjoy spectacular views of the Gulf of Mexico, Big Carlos Pass, and the sunset skies Fort Myers Beach is famous for in this beautifully...

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$209
avg per night
Fort Myers Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

STR # R250076This isn't just a beachfront condo — it's a corner end unit, and that distinction matters. The extra windows flood the space with sunlight from multiple directions, and the master bedroom gets its own private screened lanai facing Estero Bay, while the main living area's...

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Featured review

"GREAT CONDO"

We stayed here during Spring break and really enjoyed it. The beach area wasn't super busy, the condo was so nice and roomy too. Beds were comfy, everything was clean, and it was nice having chairs and...

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$292
avg per night
Fort Myers House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

In the heart of South Fort Myers, you'll find the highly desired gated community of Reflection Lakes. The community is situated on over 300 acres with 10 lakes, preserves, and close access to one of the jewels of our area, Lakes Park. The sidewalk-lined streets make evening walks easy and enjoyable....

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Featured review

"Fabulous villa! Highly recommend a visit."

This villa was great. We had a fabulous time! The pictures are true, the home looks as pictured. Very well stocked kitchen, one of the best we’ve stayed at. Location is very central, easy 20-25 minutes...

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$127
avg per night
Bonita Springs Condo
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

From the 8th floor of Building 1 at Bonita Beach & Tennis Club, the view is nothing short of spectacular — the Gulf of Mexico, the Imperial River, winding canals, and the lush tropical landscape of Bonita Beach and Bonita Springs all spread out before you. Florida sunshine pours through the...

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$136
avg per night
Fort Myers House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Venetian Pointe — a peaceful South Fort Myers retreat close to everything you love about Southwest Florida.Tucked within a quiet enclave of newer built homes and villas, the gated community of Venetian Pointe offers the perfect blend of serenity and convenience. Just minutes from...

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$148
avg per night
New
Fort Myers Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

R260413Perched on the top floor at the quiet southern end of Estero Island, this beachfront condo offers sweeping views of the Gulf, Big Carlos Pass, and the spectacular sunset skies that make Fort Myers Beach such a beloved vacation destination. Step outside to one of the island’s widest stretches...

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$199
avg per night
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Where Estero Bay meets the Gulf of Mexico—between Lovers Key State Park to the south and Estero Island, home of Fort Myers Beach to the north—you’ll find Island’s End Condominiums, one of Southwest Florida’s most enviable beachfront destinations. Perfectly positioned at the...

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$139
avg per night
Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Watch the sunset paint the sky from your open 12th floor balcony. Track the boats as they travel through Big Carlos Pass out to open water. Spot dolphins playing in Estero Bay below. This is the view — and the experience — waiting for you at this gorgeously remodeled Lovers Key Resort condominium,...

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$200
avg per night
Bonita Springs Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Day or night, the Gulf view from this 6th floor studio at Bonita Beach & Tennis Club is one you won't soon forget. Whether you're watching the morning light dance on the water from your screened lanai or catching a blazing Gulf sunset from the sofa, the view is always front and center —...

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Featured review

"Jim’s stay"

Over great view clean unit but in dire need of updates seems to be well managed we stayed last year and enjoyed the area nice short walk to beach and two decent restaurants. Pretty heavy traffic and a lot...

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$134
avg per night
Bonita Springs House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Less than 2 miles off the beach, you'll find this lovely vacation home ready to host you and your group of up to 6 in beautiful Bonita Springs. Located in a quiet residential neighborhood, you'll love the privacy this home offers, yet the proximity to some of the best dining, shopping and beaches...

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$262
avg per night
Fort Myers Beach Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

R260094The VIBE is back on Fort Myers Beach!Our beautiful Gulf Coast beaches have been renourished and are open & ready for your next beach adventure at The Gullwing Resort!We invite you to plan your next beach adventure at the resort in this homelike vacation rental. Enjoy swimming in...

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Featured review

"Better than Expected"

We had a fabulous trip to Bradenton Beach and the townhome was awesome. Ocean views and a two minute walk from doorstep to the water. I was hesitant about the property management based on past reviews but...

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$338
avg per night
Bonita Springs Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The community pools are open, the beach is right across the street, and this cheerful, thoughtfully stocked studio at Bonita Beach & Tennis Club is ready to welcome your family. With a king bed, a queen sleeper sofa, a Pack-n-Play for little ones, a granite kitchen with stainless steel appliances,...

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$126
avg per night
Fort Myers Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

OWNERS HAVE THOUGHT OF EVERYTHING!TWO ensuites - Perfect for Couples!Short walk to community pool and sun deck!Nestled in desirable south Fort Myers you'll find Sail Harbor - a guard-gated community of town homes, just minutes from our beautiful Gulf beaches, the popular vacation islands...

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$109
avg per night
Cape Coral House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your private waterfront escape in Southwest Florida — a beautifully renovated Gulf access pool home designed for sunny days, boating adventures, and unforgettable evenings by the water. Tucked into a desirable SW Cape Coral neighborhood, this stylish coastal retreat blends modern luxury...

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$247
avg per night
Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

The south/southeastern orientation of this 4th floor corner balcony gives it something the other floors can't quite match — a sweeping, angled view across Estero Bay that catches the sunrise from a uniquely beautiful direction, and keeps the water in view from an elevation that's close...

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$154
avg per night
Bonita Springs House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Vacation the Old-Florida Way is this quaint "Fish House" duplex along the shores of Little Hickory Bay.This vacation rental is a duplex and this 3 bedroom, 3 bath apartment is unit "A" sleeping up to 6 guests. The neighboring apartment is unit "B", sleeps 4, and can also...

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Featured review

"Bonita Springs 2025"

Location is excellent, close to food spots and easy to get in/out. Owner very responsive to any of our concerns/requests.Pool never really heated up - but there were several cold snaps.Bed was...

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$253
avg per night
Cape Coral House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your own private slice of modern Southwest Florida luxury — where pool days stretch into glowing evenings, game nights turn into lasting memories, and every detail has been thoughtfully designed to make vacation feel effortless.This newly constructed Southwest Cape Coral retreat was...

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$229
avg per night
Bonita Springs Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The Gulf is sparkling, the sunsets are spectacular, and the beach is just across the street. Welcome to this freshly updated studio at Bonita Beach & Tennis Club — a bright, modern retreat that's ready to welcome couples, small families, or a group of friends looking for the perfect Southwest...

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$131
avg per night
Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This vacation getaway is nothing short of wonderful!From your corner lanai you can sit and watch boat traffic passing in and out of the Gulf access canal between the Bay and local marina; step out and walk down to the paved walkway along the seawall and enjoy sightings of dolphin and manatees playing...

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$144
avg per night
Fort Myers Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Nestled in desirable south Fort Myers you'll find Sail Harbor - a private, gated community of town homes, just minutes from our beautiful Gulf beaches, the popular vacation islands of Sanibel and Captiva, and the shores of the Caloosahatchee River. As you enter the gates you'll be welcomed by...

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$113
avg per night
Cape Coral House
Sleeps 7, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to your own private slice of Southwest Florida paradise in this waterfront Cape Coral retreat designed for sunny pool days, boating adventures, and laid-back evenings by the canal. With Gulf access, a private dock, heated pool, expansive screened lanai, and plenty of room to relax both inside and...

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Featured review

"Fantastic Location"

Great amenities and the house is totally updated. Beds were fantastic, the pool was heated and the perfect temp and sheets and towels top quality. We had an amazing time and rented a pontoon boat during...

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$173
avg per night
Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

The early morning light spreads across Estero Bay in shades of amber and gold. A dolphin surfaces near the shore. A manatee drifts past the balcony. The Gulf shimmers in the distance beyond Lovers Key State Park. And you haven't left your 12th floor corner balcony yet. This is what mornings look...

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Featured review

"Great view"

Enjoyed our stay at Lovers Key Resort. The view was fantastic! The dolphins swam by every morning. Would stay again. The unit was comfortable and the people at the resort were friendly.

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$159
avg per night
Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

At the penthouse level of Lovers Key Resort, the Estero Bay sunrise arrives in full — wide, unhurried, and entirely yours from the extended private balcony. Dolphins surface in the morning stillness. Manatees drift through the shallows. Shorebirds move along the waterline. This is what the top of...

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Featured review

"Penthouse corner"

Top floor corner unit. Beautiful condo! South views good shade.Pool and restaurant close and nice. Very pleased with how everything was done!

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$153
avg per night
Cape Coral House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The area beaches are open for your enjoyment!Get ready to relax and refresh in this Southwest Cape Coral heated pool home. Whether on the water, or in the pool, your time will be spent soaking in the sun rejuvenating your yourself, your family, and your friends.At this property you will enjoy: A...

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$155
avg per night
Fort Myers House
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

An Ideal Vacation Starts Here!This beautifully renovated cottage retreat is just off palm tree lined McGregor, just minutes to the Edison Ford Estate and historic downtown. Enjoy cruising on our bikes as you explore the River District. River sunsets are just a 5-minute walk to the end of the street....

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$110
avg per night
Fort Myers Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Fort Myers Beach is back, and the beach is open to enjoy fun in the sun!While our Fort Myers Beach community continues to rebuild from the impact of recent hurricanes, and though our island paradise may look a bit different than it once did, the sun continues to shine each day and brings with it...

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$130
avg per night
New
Cape Coral House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

From the moment you step through the front door, this Southwest Cape Coral waterfront retreat invites you to slow down, settle in, and start vacation mode immediately. Tucked along a Gulf-access canal with quick boating access to the Caloosahatchee River, this beautifully updated home combines relaxed...

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$277
avg per night
Fort Myers House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Close to Southwest Florida's award winning beaches, abundant shopping, and diverse dining options you'll find a quiet little enclave of 72 homes in a peaceful, gated community called Colonial Pointe. Within the community this spacious vacation rental is ready to host your and your group of up...

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Bonita Springs House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

November & December pre-season rates have been discounted 20%. Book now to receive these already pre-season rates!Tucked away in a quiet residential neighborhood in the heart of Bonita Beach community, you'll find this charming, beautifully remodeled duplex located on a Gulf access canal....

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Cape Coral House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Come back to Southwest Florida - the area beaches are open for your enjoyment!Get ready to enjoy your Florida coastal vacation in jaw dropping style! This breathtaking home in desirable Southeast Cape Coral is ready to take your breath away and deliver everything you could hope for in a waterfront...

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Featured review

"Great place"

As described, the weather did not allow us to use the pool but would book again Host was available when messaged about additional nights of stay

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Fort Myers Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Some views are beautiful. This one is alive. From the 3rd floor corner balcony of this remodeled Lovers Key Resort luxury condo, the Estero Bay is right there — close enough to watch the morning light move across the water, and close enough to catch the dolphins, manatees, tropical fish, and birds...

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Featured review

"Nice view, nice amenities"

The location being on the south end of estero is quiet and convenient to Bonita beach and Naples. The unit was clean and had all of the necessities. You can walk to lovers key beach but is about a mile....

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Fort Myers Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • WiFi

About this property

STR #22-0469Fort Myers Beach is coming back, and the beach is open to enjoy fun in the sun! This home has been fully restored and is now accepting reservations!While our Fort Myers Beach community continues to rebuild from the impact of Hurricane Ian and though our island paradise may look a bit...

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Featured review

"Wonderful Vacation Home"

We stayed at 120 Del Mar on March 1-9. The house was cute and only a 3 minute walk to the beach. The beach cart, chairs, towels were so convenient. We enjoyed the bikes also. The kitchen had everything...

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Cape Coral House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Come back to Southwest Florida - the area beaches are open for your enjoyment!This waterfront pool/spa home offers guests to our area the classic Southwest Florida lifestyle! Located on a wide fresh-water canal near central Cape Coral, you will enjoy swimming in your own private heated pool, relaxing...

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