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Resort holiday rentals in Estero Island

Find and book unique resort rentals on Airbnb

Top-rated resort rentals in Estero Island

Guests agree: these resort rentals are highly rated for location, cleanliness and more.

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An aerial view captures the beachfront condo and surrounding area. The building's blue-topped roof contrasts with the white facade. Palm trees are seen near the coast, with the ocean stretching into the horizon under a partly cloudy sky.

Resort in Fort Myers Beach

5 out of 5 average rating, 8 reviews

Beachfront 2BR/2BA Condo on Fort Myers Beach

Direct beachfront resort with perfect sunset views. Beautiful 2 bed, 2 bath condo, featuring washer & dryers, a full kitchen, & private balconies allow you to relax each day & enjoy a morning cup of coffee or evening glass of wine. Each unit sleeps 6 & has plenty of room for everyone to spread out. Located on the north-end of the island Be-Air Beach Club is close to all the shopping & restaurants. The resort also offers a pool and complimentary grills if staying in sounds good too!

A spacious balcony with views of the ocean features a table and four chairs, alongside a lounge chair. Floor-to-ceiling glass panels allow natural light and offer an unobstructed view of the beach and water beyond.

Resort in Fort Myers Beach

Partial Ocean/Pool view Balcony 1Bdrm Suite

Ocean / Pool view at Diamondhead Beach Resort on Ft Myers Beach. One bedroom, Living room with pullout sofa, kitchenette, NEW POOL, beach chairs, workout facility, free parking covered. 10th floor overlooking the pool and the gulf of Mexico. Great beach access. Fitness Center See diamondheadfl website for more info on the hotel.

Resort in Naples

Fantastic Stay, Best Vacation! Spa Access, Pools

Ignite your getaway as we cruise from our marina to the Gulf, kayak mangroves, and lounge by five heated pools with lazy-river bliss. Just minutes from Downtown Naples, 5th Avenue shopping, white sands, and vibrant dining—so every day brings new water, wellness, and city adventures at your doorstep.

Hotel room in Fort Myers Beach

5 out of 5 average rating, 13 reviews

Beachfront and Outdoor Pool | Pets Welcome Here!

Discover serene beach bliss & vibrant nightlife steps away! We offer unforgettable sunset views along with pool parties and live entertainment. Perfect for groups of friends, family or couples craving relaxation at this sandy beachfront resort.

Guest favourite

A bedroom features a full over full bunk bed equipped with patterned bedding. A comfortable sofa is arranged nearby, accompanied by an ottoman. The space is well-lit by a ceiling fan and natural light filtered through window blinds.

Resort in Bonita Springs

5 out of 5 average rating, 10 reviews

Waterfront Gulf Access - 4 Bedroom W Heated Pool

This fabulous home is furnished with top of the line amenities throughout, and is perfect for couples or families with its spacious living areas. You can't beat the premier location! You will enjoy Gulf access and beautiful sunsets.

Guest favourite

A serene pool area is highlighted by a waterfall cascading over natural rock formations. Lush palm trees surround the space, creating a tropical ambiance. The pool features a gently curved shape with a tiled deck, inviting relaxation and leisure.

Resort in Naples

4.91 out of 5 average rating, 23 reviews

Enjoy 5 Star Luxury at the Naples Bay Resort

The Naples Bay Resort helps make your vacation perfect. The Tuscan-style resort has all the amenities you would expect in your beach destination vacation. Located in the perfect location next to the bay in the heart of Old Naples.

A cozy bedroom features a king-size bed adorned with a colorful patterned comforter and decorative pillows. Nightstands with lamps are positioned on either side of the bed. A warm orange wall adds a welcoming touch, complemented by a framed artwork above the bed. Natural light filters through partially closed vertical blinds.

Hotel room in Cape Coral

4.76 out of 5 average rating, 17 reviews

Hideaway Waterfront Resort Suite A3

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

A guest room is presented with a spacious bed featuring a checkered quilt. Nightstands with lamps are positioned on either side. A kitchenette containing a stove, fridge, and other appliances is visible. Light grey walls are adorned with framed artwork, contributing to a calm atmosphere.

Hotel room in Cape Coral

4.57 out of 5 average rating, 76 reviews

Hideaway Waterfront Resort GR A4

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

A shaded seating area is featured under a thatched roof. Two chairs with floral patterns and a small table are positioned for comfort. A few potted plants add a touch of greenery, while a painted wall in the background complements the setup.

Hotel room in Cape Coral

4.63 out of 5 average rating, 32 reviews

Hideaway Waterfront Resort Guest Suite A18

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue, fishing rods . We also have access to a local realtor, if desired.

A shaded outdoor seating area features a striped umbrella over a white table and chairs. Surrounding palm trees add greenery, while a brightly colored building is visible in the background. Flags are displayed, contributing to the resort's inviting atmosphere.

Hotel room in Cape Coral

4.42 out of 5 average rating, 24 reviews

Hideaway Waterfront Resort GS(2) A37

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue.

The living area features a comfortable sofa with decorative cushions, flanked by two side tables holding lamps. A glass-top coffee table sits in the center, complementing the light-colored walls and wooden flooring, providing a cozy and inviting space.

Hotel room in Cape Coral

4.41 out of 5 average rating, 70 reviews

Hideaway Waterfront Resort Suite A6

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue.

A bright guest room is furnished with a queen size bed covered in a patterned white and blue bedspread. A refrigerator stands nearby, and two bedside lamps illuminate the space next to the bed. A small table and chairs provide a cozy dining area.

Hotel room in Cape Coral

4.49 out of 5 average rating, 39 reviews

Hideaway Waterfront Resort GR A11

The Hideaway is an Old-Style Florida Boutique Waterfront Resort with a large, heated pool, 2500 sq ft deck that goes out over the canal, propane barbecue.

Popular amenities for resort rentals in Estero Island

Free parking on premises

Air conditioning

Family-friendly resort rentals

The image displays a sunny outdoor area featuring a heated pool surrounded by lounge chairs. Palm trees are visible, providing shade over the space. Umbrellas dot the deck area. The resort's building can be seen in the background, contributing to a relaxed atmosphere.

Hotel room in Cape Coral

4.42 out of 5 average rating, 12 reviews

Hideaway Waterfront Resort Guest Suite A36

A shaded outdoor seating area features a striped umbrella over a white table and chairs. Surrounding palm trees add greenery, while a brightly colored building is visible in the background. Flags are displayed, contributing to the resort's inviting atmosphere.

Hotel room in Cape Coral

4.42 out of 5 average rating, 24 reviews

Hideaway Waterfront Resort GS(2) A37

A relaxing pool area is surrounded by palm trees, featuring lounge chairs and white umbrellas. The inviting pool reflects the sky, while a secure fence adds a sense of privacy. The area is enhanced by tropical landscaping providing a serene atmosphere.

Hotel room in Cape Coral

4.43 out of 5 average rating, 40 reviews

Hideaway Waterfront Resort Suite A13

A guest suite features two queen-size beds dressed in shell-patterned bedding, positioned beside a bedside table with a lamp. Light enters through a window, illuminating the neutral-toned walls and wooden floor, creating a comfortable and spacious sleeping area.

Hotel room in Cape Coral

4.38 out of 5 average rating, 64 reviews

Hideaway Waterfront Resort Guest Room(2F)

The living area features a comfortable sofa with decorative cushions, flanked by two side tables holding lamps. A glass-top coffee table sits in the center, complementing the light-colored walls and wooden flooring, providing a cozy and inviting space.

Hotel room in Cape Coral

4.41 out of 5 average rating, 70 reviews

Hideaway Waterfront Resort Suite A6

A cozy bedroom features a king-size bed adorned with a colorful patterned comforter and decorative pillows. Nightstands with lamps are positioned on either side of the bed. A warm orange wall adds a welcoming touch, complemented by a framed artwork above the bed. Natural light filters through partially closed vertical blinds.

Hotel room in Cape Coral

4.76 out of 5 average rating, 17 reviews

Hideaway Waterfront Resort Suite A3

A guest room is presented with a spacious bed featuring a checkered quilt. Nightstands with lamps are positioned on either side. A kitchenette containing a stove, fridge, and other appliances is visible. Light grey walls are adorned with framed artwork, contributing to a calm atmosphere.

Hotel room in Cape Coral

4.57 out of 5 average rating, 76 reviews

Hideaway Waterfront Resort GR A4

A bright guest room is furnished with a queen size bed covered in a patterned white and blue bedspread. A refrigerator stands nearby, and two bedside lamps illuminate the space next to the bed. A small table and chairs provide a cozy dining area.

Hotel room in Cape Coral

4.49 out of 5 average rating, 39 reviews

Hideaway Waterfront Resort GR A11

Resort rentals with a pool

The image displays a sunny outdoor area featuring a heated pool surrounded by lounge chairs. Palm trees are visible, providing shade over the space. Umbrellas dot the deck area. The resort's building can be seen in the background, contributing to a relaxed atmosphere.

Hotel room in Cape Coral

4.42 out of 5 average rating, 12 reviews

Hideaway Waterfront Resort Guest Suite A36

A shaded outdoor seating area features a striped umbrella over a white table and chairs. Surrounding palm trees add greenery, while a brightly colored building is visible in the background. Flags are displayed, contributing to the resort's inviting atmosphere.

Hotel room in Cape Coral

4.42 out of 5 average rating, 24 reviews

Hideaway Waterfront Resort GS(2) A37

A comfortable living area is presented with a blue sofa adorned with decorative pillows, complemented by two side tables and matching lamps. A light-colored coffee table rests in the center, while a dining area with wooden chairs is visible in the background.

Hotel room in Cape Coral

4.14 out of 5 average rating, 14 reviews

Hideaway Waterfront Resort (ADA)

A guest suite features two queen-size beds dressed in shell-patterned bedding, positioned beside a bedside table with a lamp. Light enters through a window, illuminating the neutral-toned walls and wooden floor, creating a comfortable and spacious sleeping area.

Hotel room in Cape Coral

4.38 out of 5 average rating, 64 reviews

Hideaway Waterfront Resort Guest Room(2F)

The living area features a comfortable sofa with decorative cushions, flanked by two side tables holding lamps. A glass-top coffee table sits in the center, complementing the light-colored walls and wooden flooring, providing a cozy and inviting space.

Hotel room in Cape Coral

4.41 out of 5 average rating, 70 reviews

Hideaway Waterfront Resort Suite A6

A cozy bedroom features a king-size bed adorned with a colorful patterned comforter and decorative pillows. Nightstands with lamps are positioned on either side of the bed. A warm orange wall adds a welcoming touch, complemented by a framed artwork above the bed. Natural light filters through partially closed vertical blinds.

Hotel room in Cape Coral

4.76 out of 5 average rating, 17 reviews

Hideaway Waterfront Resort Suite A3

A guest room is presented with a spacious bed featuring a checkered quilt. Nightstands with lamps are positioned on either side. A kitchenette containing a stove, fridge, and other appliances is visible. Light grey walls are adorned with framed artwork, contributing to a calm atmosphere.

Hotel room in Cape Coral

4.57 out of 5 average rating, 76 reviews

Hideaway Waterfront Resort GR A4

A bright guest room is furnished with a queen size bed covered in a patterned white and blue bedspread. A refrigerator stands nearby, and two bedside lamps illuminate the space next to the bed. A small table and chairs provide a cozy dining area.

Hotel room in Cape Coral

4.49 out of 5 average rating, 39 reviews

Hideaway Waterfront Resort GR A11

Resort rentals with a gym

Hotel room in Naples

Ideal for Couple Stay Near Fleischmann Park | Pool

Hotel room in Fort Myers Beach

Relax in 2 Beachfront Rooms w/ Stunning Views

Hotel room in Fort Myers Beach

Steps to Beach | 2 Rooms with Outdoor Pool

Hotel room in Naples

Relaxing Room w/ Balcony Scenic Gulf Mexico View

Hotel room in Naples

Spacious 1BR w/ Living Area Scenic Gulf View

Hotel room in Fort Myers Beach

3 Peaceful Ocean Rooms w/ Balcony Breeze

A spacious Coastal View Room features two Queen beds and a comfortable sofa. A flat-screen HDTV is situated on a wooden cabinet. Large glass doors lead to a furnished balcony, providing views of the Gulf and the City of Naples.

Hotel room in Naples

Relaxing Couple Stay | Room w/ Balcony & Views

Hotel room in Fort Myers Beach

2 Seaside Resort Stays Next to Fort Myers Beach

Destinations to explore